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

Participants

Reaction Steps

In the same way as in Example 1, 250 mg (0.46 mmol) of (2R*,4R*)-4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)pentanal, 132 mg (0.63 mmol) of 5-aminoquinolone and 0.4 ml of titanium tetraethoxide are reacted to give 5-{[(2R*,4R*)-4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)pentylidene]amino}quinolin-2(1H)-one. 64 mg of imine purified by column chromatography (silica gel, hexane/ethyl acetate 0-75%) are cyclized in the same way as in Example 1 at −30° C. using 1.5 ml (1.5 mmol) of 1 M boron tribromide solution to give the desired product. Column chromatography on silica gel (hexane/ethyl acetate 0-75%) yields 52 mg of product.

Provenance & Evidence