Boron tribromide → (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol

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Reaction Steps

Under a nitrogen atmosphere, a solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-4-amine (0.8545 g, 2.161 mmol) in dichloromethane (50 mL) was cooled to about 6° C., and boron tribromide (5.4 mL of a 1 M solution in dichloromethane) was added dropwise. The reaction was heated at reflux under nitrogen for two hours and diluted with dichloromethane and methanol. The resulting solution was washed sequentially with aqueous potassium carbonate, water, and brine; dried over sodium sulfate; filtered; and concentrated under reduced pressure. The resulting solid was stirred in water overnight, isolated by filtration, purified by column chromatography on silica gel (eluting with 3% to 5% CMA in chloroform), and dried to provide 0.283 g of (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl)methanol as a tan powder, mp 164.0-165.0° C.

Provenance & Evidence