5-Amino-1,2-dihydroquinolin-2-one → 5-{[(2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one

Participants

Reaction Steps

In the same way as in Example 130, 300 mg (0.93 mmol) of (2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal, 149 mg (0.93 mmol) of 5-aminoquinolin-2(1H)-one and 0.27 ml of titanium tert-butoxide are reacted to give 5-{[(2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one. 210 mg of chromatographically purified imine (silica gel, hexane/ethyl acetate 0-80%) are cyclized in the same way as in Example 130 at −30° C. with 3.6 ml (3.6 mmol) of 1 M boron tribromide solution to give the desired product. Column chromatography on silica gel (hexane/ethyl acetate 0-100%) yields 203 mg of desired product.

Provenance & Evidence