Preparing bromo-dimethyl-dihydro-indole, useful to prepare dimethyl-(trifluoromethyl)phenyl-dihydro-indol-ylsulfonyl-methylphenoxy acetic acid, comprises reacting dimethyl-dihydro-indol-ethanone with a brominating reagent and transforming

摘要

Preparing 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole (I) and its salt, comprises reacting 1-(3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone in a solvent with a brominating reagent and subsequently optionally transforming into the salt form. Independent claims are included for: (1) preparing [4-(chlorosulfonyl)-2-methylphenoxy]acetic acid ethyl ester (II) comprising reacting (2-methylphenoxy)acetic acid ethylester in a solvent with chlorosulfonic acid; (2) preparing {4-[(5-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)sulfonyl]-2-methylphenoxy}acetic acid ethylester (III) comprising reacting (II) in a solvent mixture with 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole hydrochloride and optionally recrystallizing in a solvent or its mixture; (3) preparing {4-[(3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl)sulfonyl]-2-methylphenoxy}acetic acid ethylester (IV) comprising reacting (III) in a solvent mixture at reflux in the presence of a catalyst system, consisting of a palladium species, a phosphine ligand and a base with 4-(trifluoromethyl)phenylboronic acid; and (4) preparing {4-[(3,3-dimethyl-5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-1H-indol-1-yl)sulfonyl]-2-methylphenoxy}acetic acid (V)comprising reacting (IV) in a solvent mixture at 50[deg] C in the presence of a phase transfer catalyst with a base and optionally recrystallizing the solvent or its mixture. ACTIVITY : Cardiovascular-Gen; Antilipemic; Antiarteriosclerotic; Cardiant; Vasotropic. MECHANISM OF ACTION : Peroxisome proliferated-activated receptor delta activator.