Process for preparing 1-(6-methylpyridin-3-yl)-2-[4-methylsulphonyl)-phenyl]ethanone
US6566527B1 · kind B1 · utility
Assignees
Inventors
Key dates
| Filing date | Mar 14, 2002 |
| Grant date | May 20, 2003 |
| Priority date | — |
| Expiry date | Mar 14, 2022 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D213/50
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
A five-step process for preparing 1-(6-methylpyridin-3-yl)-2-[4-methylsulfonyl)phenyl]ethanone of formula (I): The process involves the following steps: (a) 4-(methylthio)benzyl alcohol is converted into 4-(methylthio)benzyl chloride; (b) 4-(methylthio)benzyl chloride is converted with an alkali metal cyanide into 4-(methylthio)phenylacetonitrile; (c) 4-(methylthio)phenylacetonitrile is condensed with a 6-methyinicotinic ester to give 3-[2-(2-(methylthio)phenyl)-2-cyanoacetyl](6-methyl)pyridine; (d) 3-[2-(4-(methylthio)phenyl-2-cyanoacetyl](6-methyl)pyridine is hydrolyzed and decarboxylated under acidic conditions to give 3-[2-(4-(methylthio)-phenyl)acetyl](6-methyl)pyridine is hydrolyzed and decarboxylated under acidic conditions to give 3-[2-(4-(methylthio)phenyl)acetyl(6-methyl)pyridine; and (e) 3-[2(4-(methylthio)phenyl)acetyl](6-methyl)pyridine is oxidized to give the end product. The compound of formula (I) is an intermediate for preparing COX-2 inhibitors, pharmaceutically active compounds having analgesic and antiinflammatory action.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.