5-amino-8-fluoroquinolin-2(1H)-one → 8-fluoro-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, 165 mg (0.93 mmol) of 5-amino-8-fluoroquinolin-2(1H)-one and 0.58 ml of titanium tert-butoxide are reacted to give 8-fluoro-5-{[(2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one. 280 mg of chromatographically purified imine (silica gel, hexane/ethyl acetate 0-75%) are cyclized in the same way as in Example 130 at −30° C. with 4.6 ml (4.6 mmol) of 1 M boron tribromide solution to give the desired product. Column chromatography on silica gel (hexane/ethyl acetate 0-100%) yields 230 mg of desired product.

Provenance & Evidence