5-amino-7-fluoroquinolin-2(1H)-one → 7-fluoro-5-{[(2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]-amino}quinolin-2(1H)-one

In the same way as in Example 130, 271 mg (0.51 mmol) of (2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal, 90 mg (0.51 mmol) of 5-amino-7-fluoroquinolin-2(1H)-one and 0.32 ml (1.02 mmol) of titanium tert-butoxide are reacted to give 7-fluoro-5-{[(2R,4R)-4-(4-fluoro-2-methoxy-3-methylphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]-amino}quinolin-2(1H)-one. 320 mg of crude imine are cyclized in the same way as in Example 130 at −30° C. with 4.1 ml (4.1 mmol) of 1 M boron tribromide solution to give the desired product. Column chromatography on silica gel (hexane/ethyl acetate 50%) yields 165 mg of desired product.