5-Quinolinamine, 2-methyl- → 4-(3-Fluoro-2-methoxyphenyl)-1-[(2-methylquinolin-5-yl)imino]-5-methyl-2-(trifluoromethyl)hexan-2-ol

Beteiligte Stoffe

Reaktionsschritte

In the same way as in Example 61, 200 mg (0.62 mmol) of 4-(3-fluoro-2-methoxyphenyl)-2-hydroxy-5-methyl-2-(trifluoromethyl)hexanal, 125 mg (0.80 mmol) of 5-amino-2-methylquinoline and 0.3 ml of titanium tetraethoxide are reacted to give 4-(3-fluoro-2-methoxyphenyl)-1-[(2-methylquinolin-5-yl)imino]-5-methyl-2-(trifluoromethyl)hexan-2-ol. 229 mg of imine purified by column chromatography (silica gel, hexane/ethyl acetate 0-35%) are cyclized in the same way as in Example 61 at −20° C. with 5 ml (5 mmol) of 1 M boron tribromide solution in dichloromethane to give the desired product. Column chromatography on silica gel (hexane/2-propanol 0-15%) and subsequent preparative HPLC (SunFire C18, water/methanol) yield 11 mg of product.

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