WO2008139057A3 - Procede de preparation de 2-(n-butyl)-3-(4-hydroxybenzoyl)-5-nitrobenzofurane - Google Patents
Procede de preparation de 2-(n-butyl)-3-(4-hydroxybenzoyl)-5-nitrobenzofurane Download PDFInfo
- Publication number
- WO2008139057A3 WO2008139057A3 PCT/FR2008/000472 FR2008000472W WO2008139057A3 WO 2008139057 A3 WO2008139057 A3 WO 2008139057A3 FR 2008000472 W FR2008000472 W FR 2008000472W WO 2008139057 A3 WO2008139057 A3 WO 2008139057A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- preparing
- nitrobenzofurane
- hydroxybenzoyl
- butyl
- derivative
- Prior art date
Links
- ZJZKLBXEGZKOBW-UHFFFAOYSA-N (2-butyl-5-nitro-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=C(O)C=C1 ZJZKLBXEGZKOBW-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- CGHIBGNXEGJPQZ-UHFFFAOYSA-N 1-hexyne Chemical compound CCCCC#C CGHIBGNXEGJPQZ-UHFFFAOYSA-N 0.000 abstract 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 abstract 1
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 150000005342 methoxybenzoic acids Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Procédé de préparation de 2-(n-butyl)-3-(4-hydroxybenzoyl)-5-nitrobenzofurane à partir du 4-nitrophénol, dans lequel on prépare le dérivé 2-iodo-(ou 2-bromo)-4-nitrophénol, puis on effectue une réaction de couplage de Sonogashira par action de l'hexyne, suivie de Pacylation par un dérivé réactif de l'acide méthoxybenzoïque et de la déméthylation du dérivé 4-méthoxybenzoïque obtenu.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0702544 | 2007-04-06 | ||
FR0702544A FR2914644B1 (fr) | 2007-04-06 | 2007-04-06 | Procede de preparation de 2-(n-butyl)-3-(4-hydroxybenzoyl) -5-nitrobenzofurane |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2008139057A2 WO2008139057A2 (fr) | 2008-11-20 |
WO2008139057A3 true WO2008139057A3 (fr) | 2009-01-08 |
Family
ID=38714169
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2008/000472 WO2008139057A2 (fr) | 2007-04-06 | 2008-04-04 | Procede de preparation de 2-(n-butyl)-3-(4-hydroxybenzoyl)-5-nitrobenzofurane |
Country Status (2)
Country | Link |
---|---|
FR (1) | FR2914644B1 (fr) |
WO (1) | WO2008139057A2 (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3195862A1 (fr) | 2008-04-17 | 2017-07-26 | Sanofi | Utilisation de la dronedarone dans la preparation d'un medicament utilise pour prevenir un episode cardiovasculaire menant a l'hospitalisation ou prevenir la fibrillation auriculaire |
US8602215B2 (en) | 2010-06-30 | 2013-12-10 | Sanofi | Methods for reducing the risk of an adverse dronedarone/beta-blockers interaction in a patient suffering from atrial fibrillation |
CN101948455B (zh) * | 2010-10-18 | 2012-11-14 | 山东邹平大展新材料有限公司 | 一种2-正丁基-3-(4-羟基苯甲酰基)-5-硝基苯并呋喃的制备方法 |
CN110590722B (zh) * | 2019-10-22 | 2022-11-04 | 温州大学 | 2-三氟甲基苯并呋喃衍生物的合成方法 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0471609A1 (fr) * | 1990-08-06 | 1992-02-19 | Sanofi | Dérivés de Benzofuranne, Benzothiophène, Indole ou Indolizine, leur procédé de préparation ainsi que les compositions les contenant |
WO1996005190A1 (fr) * | 1994-08-11 | 1996-02-22 | Karo Bio Ab | Derives de 3-benzoyle benzofurane en tant qu'antagonistes de l'hormone thyroidienne |
WO2003040120A1 (fr) * | 2001-11-08 | 2003-05-15 | Isp Investments Inc. | Procede de preparation de dronedarone |
WO2005066149A1 (fr) * | 2003-12-24 | 2005-07-21 | Clariant (France) | Procede d'elaboration de n-alkyle-2(hydroxy-4 benzoyle)-3 benzofuranes, et intermediaires correspondants |
FR2877341A1 (fr) * | 2004-11-02 | 2006-05-05 | Rhodia Chimie Sa | Procede d'acylation d'un compose aromatique |
-
2007
- 2007-04-06 FR FR0702544A patent/FR2914644B1/fr not_active Expired - Fee Related
-
2008
- 2008-04-04 WO PCT/FR2008/000472 patent/WO2008139057A2/fr active Application Filing
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0471609A1 (fr) * | 1990-08-06 | 1992-02-19 | Sanofi | Dérivés de Benzofuranne, Benzothiophène, Indole ou Indolizine, leur procédé de préparation ainsi que les compositions les contenant |
WO1996005190A1 (fr) * | 1994-08-11 | 1996-02-22 | Karo Bio Ab | Derives de 3-benzoyle benzofurane en tant qu'antagonistes de l'hormone thyroidienne |
WO2003040120A1 (fr) * | 2001-11-08 | 2003-05-15 | Isp Investments Inc. | Procede de preparation de dronedarone |
WO2005066149A1 (fr) * | 2003-12-24 | 2005-07-21 | Clariant (France) | Procede d'elaboration de n-alkyle-2(hydroxy-4 benzoyle)-3 benzofuranes, et intermediaires correspondants |
FR2877341A1 (fr) * | 2004-11-02 | 2006-05-05 | Rhodia Chimie Sa | Procede d'acylation d'un compose aromatique |
Also Published As
Publication number | Publication date |
---|---|
FR2914644A1 (fr) | 2008-10-10 |
FR2914644B1 (fr) | 2009-06-05 |
WO2008139057A2 (fr) | 2008-11-20 |
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