5-amino-8-fluoroquinolin-2(1H)-one → 8-fluoro-5-{[4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one

Participants

Reaction Steps

In the same way as in Example 29, 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexanal and 5-amino-8-fluoroquinolin-2(1H)-one are condensed to give 8-fluoro-5-{[4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-2-(trifluoromethyl)hexylidene]amino}quinolin-2(1H)-one. Reaction with 1 M boron tribromide solution after column chromatography on silica gel (hexane/ethyl acetate 33-100%) and preparative HPLC yield not only the desired product but also the methyl ether cleaved compounds Example 35 and 44.

Provenance & Evidence