5-Bromo-2-chloropyrimidine → (-)-2-[1-(5-Cyanopyrimidine-2-yl)piperidin-4-yl]-4-(4,4-difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-7,7-dimethyl-5,6,7,8-tetrahydroquinoline-5-ol

Participants

Reaction Steps

Reactions similar to those of the first step of Example 2 and Example 38 were performed except for using 2-chloropyrimidine-5-carbonitrile, which was synthesized by the method described in A. Takamizawa et al., Journal of Organic Chemistry, 1964, Vol. 29, pp. 1740-1742, instead of 5-bromo-2-chloropyrimidine, and from 78 mg (0.12 mmol) of (−)-4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-2-(piperidin-4-yl)-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 10, 60 mg of the title compound was obtained as a white solid (yield: 79%).

Provenance & Evidence