Methanol → HCID 59026688, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, a solution of 2-(ethoxymethyl)-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-4-amine (0.9923 g, 2.377 mmol) in 1,2-dichloroethane (55 mL) was cooled to about 0° C., and boron tribromide (5.9 mL of a 1 M solution in dichloromethane) was added dropwise. After the reaction was stirred cold for 30 minutes, it was heated at 50° C. for six hours. An analysis by HPLC indicated the reaction was incomplete, and the reaction was again cooled to about 0° C., and additional boron tribromide (1.5 mL) was added dropwise. After the reaction was stirred cold for ten minutes, it was heated at 50° C. for 16 hours. Methanol (30 mL) was added, and the reaction mixture was allowed to cool to room temperature. After 16 hours, the precipitate from the reaction was isolated by filtration and washed sequentially with aqueous potassium hydroxide (30 mL of 1 N), methanol (15 mL), and diethyl ether (15 mL). The solid was then triturated with boiling acetonitrile and isolated by hot filtration to provide 0.161 g of (4-amino-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinolin-2-yl)methanol as a white powder, mp 262.0-263.0° C.

Provenance & Evidence