WO2008111474A1 - Process for production of indole compound - Google Patents
Process for production of indole compound Download PDFInfo
- Publication number
- WO2008111474A1 WO2008111474A1 PCT/JP2008/054016 JP2008054016W WO2008111474A1 WO 2008111474 A1 WO2008111474 A1 WO 2008111474A1 JP 2008054016 W JP2008054016 W JP 2008054016W WO 2008111474 A1 WO2008111474 A1 WO 2008111474A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- indole compound
- oco
- amount
- active carbon
- compound
- Prior art date
Links
- -1 indole compound Chemical class 0.000 title abstract 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 title abstract 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 229960000905 indomethacin Drugs 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/18—Carbon
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Indole Compounds (AREA)
- Carbon And Carbon Compounds (AREA)
- Catalysts (AREA)
Abstract
Disclosed is a process for producing an indole compound by contacting an indoline compound with oxygen in the presence of a catalyst comprising active carbon which satisfies the requirement represented by the formula (I). 4000<S×(Oco) (I) [wherein S represents a BET specific surface area (m2/g); and Oco represents an amount (expressed by wt%) of the surface oxygen released in the form of carbon monoxide by heating relative to the amount of active carbon.] The process enables to produce an indole compound which is useful as the skeletal component for a pharmaceutical agent (e.g., indomethacin) or a dye at low cost and in a safe and efficient manner.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007-059414 | 2007-03-09 | ||
JP2007059414A JP2008222576A (en) | 2007-03-09 | 2007-03-09 | Method for producing indole compound |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008111474A1 true WO2008111474A1 (en) | 2008-09-18 |
Family
ID=39759416
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2008/054016 WO2008111474A1 (en) | 2007-03-09 | 2008-03-06 | Process for production of indole compound |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP2008222576A (en) |
WO (1) | WO2008111474A1 (en) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
CN106432040A (en) * | 2016-08-09 | 2017-02-22 | 中钢集团鞍山热能研究院有限公司 | Environment-friendly synthesis method for medicine intermediate 5-bromoindole |
CN106966950A (en) * | 2017-04-17 | 2017-07-21 | 兰州大学 | A kind of preparation method of the bromo indole of pharmaceutical intermediate 5 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51110561A (en) * | 1975-03-25 | 1976-09-30 | Mitsui Toatsu Chemicals | INDOOR USEIZOHO |
JP2005145859A (en) * | 2003-11-13 | 2005-06-09 | Nippon Steel Chem Co Ltd | Dehydrogenation method and method for producing aromatic heterocyclic compound |
WO2006028035A1 (en) * | 2004-09-06 | 2006-03-16 | Japan Envirochemicals, Ltd. | Oxidation reaction catalyst and process for producing compound using the same |
-
2007
- 2007-03-09 JP JP2007059414A patent/JP2008222576A/en active Pending
-
2008
- 2008-03-06 WO PCT/JP2008/054016 patent/WO2008111474A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS51110561A (en) * | 1975-03-25 | 1976-09-30 | Mitsui Toatsu Chemicals | INDOOR USEIZOHO |
JP2005145859A (en) * | 2003-11-13 | 2005-06-09 | Nippon Steel Chem Co Ltd | Dehydrogenation method and method for producing aromatic heterocyclic compound |
WO2006028035A1 (en) * | 2004-09-06 | 2006-03-16 | Japan Envirochemicals, Ltd. | Oxidation reaction catalyst and process for producing compound using the same |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
CN106432040A (en) * | 2016-08-09 | 2017-02-22 | 中钢集团鞍山热能研究院有限公司 | Environment-friendly synthesis method for medicine intermediate 5-bromoindole |
CN106432040B (en) * | 2016-08-09 | 2019-02-19 | 中钢集团鞍山热能研究院有限公司 | A kind of green synthesis method of medicine intermediate 5- bromo indole |
CN106966950A (en) * | 2017-04-17 | 2017-07-21 | 兰州大学 | A kind of preparation method of the bromo indole of pharmaceutical intermediate 5 |
Also Published As
Publication number | Publication date |
---|---|
JP2008222576A (en) | 2008-09-25 |
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