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WO2018025590A1 - Procédé de production d'un composé hétérocyclique contenant de l'azote et composé hétérocyclique contenant de l'azote - Google Patents

Procédé de production d'un composé hétérocyclique contenant de l'azote et composé hétérocyclique contenant de l'azote Download PDF

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Publication number
WO2018025590A1
WO2018025590A1 PCT/JP2017/025102 JP2017025102W WO2018025590A1 WO 2018025590 A1 WO2018025590 A1 WO 2018025590A1 JP 2017025102 W JP2017025102 W JP 2017025102W WO 2018025590 A1 WO2018025590 A1 WO 2018025590A1
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compound
general formula
structure represented
nitrogen
atom
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PCT/JP2017/025102
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English (en)
Japanese (ja)
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杉田　修一
加藤　栄作
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コニカミノルタ株式会社
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Priority to JP2018531802A priority Critical patent/JP7071919B2/ja
Publication of WO2018025590A1 publication Critical patent/WO2018025590A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods

Definitions

  • the present invention relates to a method for producing a nitrogen-containing heterocyclic compound and a nitrogen-containing heterocyclic compound. More specifically, the present invention relates to a method for producing a nitrogen-containing heterocyclic compound that can provide a nitrogen-containing heterocyclic compound useful as a material for an organic electroluminescence device in a high yield.
  • the present invention has been made in view of the above problems and circumstances, and the solution to the problem is to provide a method for producing a nitrogen-containing heterocyclic compound having high yield and high purity and excellent production suitability and environmental suitability. That is.
  • the present inventor made a high yield by reacting a compound having a specific structure with bromine in the presence of silver salt, sulfuric acid and carboxylic acid.
  • the inventors have found that a method for producing a nitrogen-containing heterocyclic compound having a specific structure that is highly pure and excellent in production suitability and environmental suitability can be obtained, and the present invention has been achieved. That is, the said subject of this invention is solved by the following means.
  • a compound having the structure represented by the following general formula [1] is reacted with bromine in the presence of silver salt, sulfuric acid and carboxylic acid to synthesize a compound having the structure represented by the following general formula [2].
  • a method for producing a nitrogen-containing heterocyclic compound In the formula, X represents an oxygen atom or a sulfur atom.
  • a 1 to A 4 each represents a nitrogen atom or CR. However, at least one of A 1 to A 4 is a nitrogen atom.
  • R 1 to R 3 each represents a hydrogen atom or a substituent.
  • the compound having a structure represented by the general formula [1] is a compound having a structure represented by the following general formula [3], and a compound having a structure represented by the general formula [2]
  • X represents an oxygen atom or a sulfur atom.
  • R 1 to R 6 each represents a hydrogen atom or a substituent.
  • the compound having a structure represented by the general formula [1] is a compound having a structure represented by the following general formula [5], and a compound having a structure represented by the general formula [2]
  • claim which is a compound which has a structure represented by following General formula [6].
  • X represents an oxygen atom or a sulfur atom.
  • X 1 represents a bromine atom or an iodine atom.
  • R 1 to R 5 each represents a hydrogen atom or a substituent.
  • a nitrogen-containing heterocyclic compound which is a compound having a structure represented by the following general formula [6].
  • X represents an oxygen atom or a sulfur atom.
  • X 1 represents a bromine atom or an iodine atom.
  • R 1 to R 5 each represents a hydrogen atom or a substituent.
  • the method for producing a nitrogen-containing heterocyclic compound of the present invention comprises reacting a compound having the structure represented by the general formula [1] with bromine in the presence of a silver salt, sulfuric acid and carboxylic acid, A compound having a structure represented by [2] is synthesized. Moreover, the nitrogen-containing heterocyclic compound of the present invention is a compound having a structure represented by the general formula [6].
  • the compound having the structure represented by the general formula [1] is a compound having the structure represented by the general formula [3], and the compound having the structure represented by the general formula [2]. Is preferably a compound having a structure represented by the general formula [4].
  • the compound having the structure represented by the general formula [1] is a compound having the structure represented by the general formula [5], and the compound having the structure represented by the general formula [2]. Is preferably a compound having a structure represented by the general formula [6].
  • the compound represented by the general formula [8] is obtained by reacting a compound having the structure represented by the general formula [2] with a compound having a structure represented by the general formula [7] and further reacting with an acid. It is preferable to produce a compound having the structure
  • ⁇ is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.
  • X represents an oxygen atom or a sulfur atom.
  • a 1 to A 4 each represent a nitrogen atom or CR. However, at least one of A 1 to A 4 is a nitrogen atom.
  • R and R 1 to R 3 each represent a hydrogen atom or a substituent.
  • X represents an oxygen atom or a sulfur atom, and among the groups represented by X, an oxygen atom is particularly preferable.
  • a 1 ⁇ A 4 represent a nitrogen atom or a CR. However, at least one of A 1 to A 4 is a nitrogen atom, preferably one is a nitrogen atom, and particularly preferably A 1 is a nitrogen atom.
  • Examples of the substituent represented by R and R 1 to R 3 include an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an acylamino group, a sulfonamide group, an alkylthio group, an arylthio group, a halogen atom, a heterocyclic ring ( For example, dibenzofuran ring, azadibenzofuran ring, etc.) group, sulfonyl group, sulfinyl group, phosphonyl group, acyl group, carbamoyl group, sulfamoyl group, cyano group, alkoxy group, aryloxy group, heterocyclic oxy group, siloxy group, acyloxy group, Carbamoyloxy, amino, alkylamino, imide, ureido, sulfamoylamino, alkoxycarbonylamino, alkoxycarbonylamin
  • any of the above substituents may be further substituted with a substituent, for example, an alkyl group, a cycloalkyl group, an alkenyl group, an aryl group, an acylamino group, a sulfonamido group, an alkylthio group, an arylthio group, a halogen atom, Heterocyclic group, sulfonyl group, sulfinyl group, phosphonyl group, acyl group, carbamoyl group, sulfamoyl group, cyano group, alkoxy group, aryloxy group, heterocyclic oxy group, siloxy group, acyloxy group, carbamoyloxy group, amino group, Examples include alkylamino groups, imide groups, ureido groups, sulfamoylamino groups, alkoxycarbonylamino groups, alkoxycarbonylamino groups, aryloxycarbonylamino
  • the amount of bromine used in the present invention is preferably within a range of 0.8 to 1.3 times, particularly preferably 0.9, in terms of molar ratio to the compound having the structure represented by the general formula [1]. It is in the range of -1.2 times.
  • silver salt used in the present invention examples include silver acetate, silver sulfate, silver carbonate, silver nitrate, silver phosphate, silver oxide, and silver halide. Of these, silver sulfate is preferred.
  • the amount of silver salt used in the present invention is preferably in the range of 0.3 to 3 mol, particularly preferably 0.5 to 1.5 mol, relative to 1 mol of the compound having the structure represented by the general formula [1]. Within range.
  • the amount of sulfuric acid used in the present invention is preferably in the range of 1 to 5 mL, particularly preferably in the range of 1 to 3 mL, with respect to 1 g of the compound having the structure represented by the general formula [1].
  • carboxylic acid used in the present invention examples include acetic acid, propionic acid, butyric acid, pivalic acid, benzoic acid and the like, and acetic acid is particularly preferable.
  • Advantages of using carboxylic acid are that the reaction becomes mild and can suppress the formation of by-products, that stirring is good and that production is excellent, and that carboxylic acid is a weak acid, so it is not necessary to neutralize waste liquid and environmental suitability. For example, it is excellent.
  • the amount of the carboxylic acid used in the present invention is preferably in the range of 5 to 50 mL, particularly preferably in the range of 10 to 30 mL, with respect to 1 g of the compound having the structure represented by the general formula [1].
  • the reaction rate (measured by HPLC) is improved and the yield can be improved.
  • the yield is preferably 75% or more, and particularly preferably 80% or more.
  • the amount of water used in the present invention is preferably in the range of 1 to 5 mL, particularly preferably in the range of 1 to 3 mL with respect to 1 g of the compound having the structure represented by the general formula [1].
  • the compound having a structure represented by the general formula [1] is a compound having a structure represented by the following general formula [3], and a compound having a structure represented by the general formula [2] Is preferably a compound having a structure represented by the following general formula [4].
  • X represents an oxygen atom or a sulfur atom.
  • R 1 to R 6 each represent a hydrogen atom or a substituent.
  • Substituents represented by R 1 ⁇ R 6 has the general formula [1] and can use the same as the substituent represented by R 1 ⁇ R 6 of [2], further be substituted with a substituent The same applies to the points that may be used.
  • the compound having a structure represented by the general formula [1] is a compound having a structure represented by the following general formula [5], and a compound having a structure represented by the general formula [2]
  • a compound having a structure represented by the following general formula [6] is preferable.
  • the nitrogen-containing heterocyclic compound of the present invention is a compound having a structure represented by the following general formula [6].
  • R 1 to R 5 can be the same as the substituents represented by R 1 to R 6 in the general formulas [1] and [2], and are further substituted with substituents. The same applies to the points that may be used.
  • X 1 represents a bromine atom or an iodine atom, and among the groups represented by X 1 , preferred is an iodine atom.
  • the compound represented by the general formula [2] is reacted with a compound having the structure represented by the following general formula [7], and further reacted with an acid, thereby being represented by the following general formula [8]. It is preferable to produce a compound having the structure
  • X represents an oxygen atom or a sulfur atom.
  • a 1 to A 4 each represent a nitrogen atom or CR. However, at least one of A 1 to A 4 is a nitrogen atom.
  • R and R 1 to R 3 represent a hydrogen atom or a substituent.
  • R 7 represents an alkyl group or an aryl group. The substituents represented by R, R 1 to R 3 and R 7 may be the same as the substituents represented by R 1 to R 6 in the general formulas [1] and [2]. The point which may be substituted by group is also the same.
  • Examples of the alkyl group represented by R 7 include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a pentyl group, and an octyl group.
  • Examples of the aryl group represented by R 7 include a phenyl group, a biphenyl group, and a terphenyl group.
  • the acid used after reacting the compound having the structure represented by the general formula [2] and the compound having the structure represented by the general formula [7] is not particularly limited, but sulfuric acid, concentrated hydrochloric acid, phosphoric acid , Acetic acid, tosylic acid or methanesulfonic acid.
  • the reaction temperature is usually preferably in the range of 0 to 40 ° C., particularly preferably in the range of 10 to 30 ° C.
  • Pd catalyst When the compound having the structure represented by the general formula [2] and the compound having the structure represented by the general formula [7] are reacted, it is preferable to use a Pd catalyst or a Cu catalyst, and particularly preferably a Pd catalyst.
  • the Pd catalyst that can be used include, but are not limited to, PdCl 2 , Pd (OAc) 2 , Pd (pph 3 ) 4 , PdCl 2 (dppf), Pd (dba) 2 , and Pd / C.
  • a ligand may be used in combination with a Pd catalyst.
  • a trialkylphosphine for example, tributylphosphine, tri-t-butylphosphine, tricyclohexylphosphine
  • a phosphine having at least one aryl group for example, triphenylphosphine, SPhos, XPhos) , T-BuXPhos etc.
  • phosphine having one aryl group is preferable, and t-BuXPhos is particularly preferable.
  • Cu catalyst As it can be used as a Cu catalyst is not particularly limited CuCl, CuCl 2, CuBr, CuBr 2, CuI, CuI 2, CuO, Cu 2 O, CuSO 4, Cu 2 SO 4, CuOCOCH 3, Cu (OCOCH 3 ) 2 etc. are mentioned. Of these, CuI and Cu 2 O are particularly preferred.
  • a ligand may be used in combination with a Cu catalyst.
  • quaternary ammonium salts tetra-n-butylammonium fluoride (TBAF), tetraethylammonium iodide), 2,2′-bipyridine, tri (t-butyl) phosphine, 1,2-bis (diphenylphosphino) ethane (DPPE), 1,3-bis (diphenylphosphino) propane (DPPP), 1,4-bis (diphenylphosphino) butane (DPPB), 1,1′- Bis (diphenylphosphino) ferrocene (DPPF), tricyclohexylphosphine (PCy 3 ), aryl alcohols (eg 2-phenylphenol, 1-naphthol, 2,6-dimethylphenol, salicylaldoxime, N, N-diethylsalicyl) Amide, 8-hydroxyquinoline, etc.), alkyl Mines (eg 2- (dimethylamino) ethanol
  • Synthesis example 1 (comparative example) ⁇ Synthesis of Exemplary Compound B-1 >> 34 g (0.2 mol) of exemplary compound A-1, 35 mL of sulfuric acid and 100 mL of water were mixed, and 65 g of silver sulfate and 48 g (0.3 mol) of bromine were added. Since the reaction did not proceed at room temperature, the mixture was heated to reflux for 5 hours, but stirring was insufficient. 80 mL of water was added and 84 g of sodium carbonate was added over 10 minutes. Extraction was performed with 5000 mL of a 1: 1 mixture of toluene / tetrahydrofuran (THF), and the solvent was removed. After refluxing with methanol, the crystals were filtered and dried to obtain 14.9 g of Exemplified Compound B-1 (yield 30%, purity 90.5%).
  • THF toluene / tetrahydrofuran
  • Synthesis Example 2 (present invention) ⁇ Synthesis of Exemplary Compound B-1 >> 34 g (0.2 mol) of Exemplified Compound A-1, 35 mL of sulfuric acid, 10 mL of water and 340 mL of acetic acid were mixed, and 65 g of silver sulfate and 35 g (0.22 mol) of bromine were added. The reaction proceeded at room temperature and stirring was sufficient. Stirring was carried out for 3 hours. 300 mL of water was added and 84 g of sodium carbonate was added over 10 minutes. Extraction with 800 mL of THF removed the solvent. After heating to reflux with methanol, the crystals were filtered and dried to obtain 40.1 g of Exemplified Compound B-1 (yield 81%, purity 98.4%).
  • Synthesis example 3 (comparative example) ⁇ Synthesis of Exemplary Compound B-1 >> When the acetic acid of Synthesis Example 2 was replaced with the same amount of water, stirring was sufficient but the reaction did not proceed.
  • Synthesis example 4 (comparative example) ⁇ Synthesis of Exemplary Compound B-1 >> 34 g (0.2 mol) of Exemplified Compound A-1, 375 mL of sulfuric acid and 10 mL of water were mixed, and 65 g of silver sulfate and 35 g (0.22 mol) of bromine were added. The reaction proceeded at room temperature and stirring was insufficient, but stirring was performed for 3 hours. 3000 mL of water was added and 895 g of sodium carbonate was added over 1 hour. Extraction with 5000 mL of THF removed the solvent. After heating to reflux with methanol, the crystals were filtered and dried to obtain 32 g of Exemplified Compound B-1 (yield 65%, purity 90.1%).
  • Synthesis Example 5 (present invention) ⁇ Synthesis of Exemplary Compound B-4 >> 50 g (0.169 mol) of exemplary compound A-4, 100 mL of sulfuric acid, 50 mL of water and 1.2 L of acetic acid were mixed, and 52 g of silver sulfate was further added. 29.7 g (0.186 mol) of bromine was added dropwise over 10 minutes, and the mixture was further stirred for 3 hours. 500 mL of water was added and 240 g of sodium carbonate was added over 1 hour. The crystals were collected by filtration and dried. It was dissolved in 5 L of THF to remove insoluble matters. After concentration under reduced pressure, the mixture was heated to reflux with methanol, and the crystals were collected by filtration and dried to obtain 53.7 g of Exemplified Compound B-4 (yield 85%, purity 97.0%).
  • Synthesis Example 6 (present invention) ⁇ Synthesis of Exemplary Compound B-4 >> 50 g (0.169 mol) of exemplary compound A-4, 100 mL of sulfuric acid, 50 mL of water, and 1.2 L of propionic acid were mixed, and 52 g of silver sulfate was further added. 29.7 g (0.186 mol) of bromine was added dropwise over 10 minutes, and the mixture was further stirred for 3 hours. 500 mL of water was added and 240 g of sodium carbonate was added over 1 hour. The crystals were collected by filtration and dried. It was dissolved in 5 L of THF to remove insoluble matters. After concentration under reduced pressure, the mixture was heated to reflux with methanol, and the crystals were collected by filtration and dried to obtain 51.2 g of Exemplified Compound B-4 (yield 81%, purity 96.7%).
  • Synthesis Example 7 (present invention) ⁇ Synthesis of Exemplary Compound B-4 >> 50 g (0.169 mol) of exemplary compound A-4, 100 mL of sulfuric acid, 50 mL of water and 1.2 L of acetic acid were mixed, and 28 g of silver acetate was further added. 29.7 g (0.186 mol) of bromine was added dropwise over 10 minutes, and the mixture was further stirred for 3 hours. 500 mL of water was added and 240 g of sodium carbonate was added over 1 hour. The crystals were collected by filtration and dried. It was dissolved in 5 L of THF to remove insoluble matters. After concentration under reduced pressure, the mixture was heated to reflux with methanol, and the crystals were collected by filtration and dried to obtain 51.2 g of Exemplified Compound B-4 (yield 81%, purity 96.0%).
  • Synthesis Example 8 (Comparative Example) ⁇ Synthesis of Exemplary Compound B-4 >> The acetic acid in Synthesis Example 5 was replaced with the same amount of water, but the reaction did not proceed.
  • Synthesis Example 9 (present invention) ⁇ Synthesis of Exemplified Compound D-2 >> 8.9 g (0.0214 mol) of Exemplified Compound B-2, 5.0 g (0.0427 mol) of Exemplified Compound C-5, 4.1 g of t-C 4 H 9 ONa, and 160 mL of THF were added under a nitrogen stream. And stirred for 20 minutes. To this suspension, 1.3 g of Pd (dba) 2 and 0.7 g of t-BuXPhos were added and refluxed for 2 hours. After adding 600 mL of THF and removing insolubles, the mixture was concentrated under reduced pressure.
  • the method for producing a nitrogen-containing heterocyclic compound of the present invention can be suitably used for producing, for example, a nitrogen-containing heterocyclic compound used as a material for an organic electroluminescence device.
  • the nitrogen-containing heterocyclic compound manufactured by the manufacturing method of the nitrogen-containing heterocyclic compound of this invention and the nitrogen-containing heterocyclic compound of this invention can be used suitably as an organic electroluminescent element material, for example.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

La présente invention traite le problème de fournir un procédé de production, avec un rendement élevé, d'un composé hétérocyclique contenant de l'azote ayant une pureté élevée, une aptitude à la production supérieure, et une adéquation environnementale supérieure. Le procédé de production d'un composé hétérocyclique contenant de l'azote selon la présente invention comprend la synthèse d'un composé ayant une structure représentée par la formule générale [2], en faisant réagir un composé ayant une structure représentée par la formule générale [1] avec du brome en présence d'un sel d'argent, d'acide sulfurique et d'un acide carboxylique.
PCT/JP2017/025102 2016-08-02 2017-07-10 Procédé de production d'un composé hétérocyclique contenant de l'azote et composé hétérocyclique contenant de l'azote WO2018025590A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006132295A1 (fr) * 2005-06-09 2006-12-14 Dainippon Sumitomo Pharma Co., Ltd. Regulateur de recepteur d’aldosterone
WO2009008100A1 (fr) * 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Matériau pour élément à électroluminescence organique, et élément à électroluminescence organique préparé à l'aide du matériau
JP2011084531A (ja) * 2009-10-19 2011-04-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
WO2013038650A1 (fr) * 2011-09-13 2013-03-21 出光興産株式会社 Dérivé aromatique hétérocyclique condensé, matériau pour élément électroluminescent organique, et élément électroluminescent organique l'utilisant
JP2014533237A (ja) * 2011-08-02 2014-12-11 上海唐▲潤▼医▲葯▼科技有限公司 Ｈｃｖプロテアーゼ阻害剤

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3475868B2 (ja) * 1999-09-17 2003-12-10 松下電器産業株式会社 磁気抵抗効果型薄膜磁気ヘッド

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006132295A1 (fr) * 2005-06-09 2006-12-14 Dainippon Sumitomo Pharma Co., Ltd. Regulateur de recepteur d’aldosterone
WO2009008100A1 (fr) * 2007-07-10 2009-01-15 Idemitsu Kosan Co., Ltd. Matériau pour élément à électroluminescence organique, et élément à électroluminescence organique préparé à l'aide du matériau
JP2011084531A (ja) * 2009-10-19 2011-04-28 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP2014533237A (ja) * 2011-08-02 2014-12-11 上海唐▲潤▼医▲葯▼科技有限公司 Ｈｃｖプロテアーゼ阻害剤
WO2013038650A1 (fr) * 2011-09-13 2013-03-21 出光興産株式会社 Dérivé aromatique hétérocyclique condensé, matériau pour élément électroluminescent organique, et élément électroluminescent organique l'utilisant

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