Ethyl orthoformate → 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline

Participants

Reaction Conditions

Reaction Steps

Pyridine hydrochloride (3 mg, 0.02 mmol) and triethyl orthoformate (0.3 mL, 1.7 mmol) were added to a solution of 2-chloro-N4-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}quinoline-3,4-diamine (0.4294 g, 1.164 mmol) in toluene (10 mL), and the reaction was heated at 110° C. for 16 hours. A solid was present and was isolated by filtration. The filtrate was concentrated under reduced pressure and triturated with diethyl ether to provide a solid. The two solids were combined and purified by column chromatography on silica gel (eluting with 1:1 ethyl acetate:hexane) to provide 0.259 g of 4-chloro-1-{[3-(4-fluorophenyl)isoxazol-5-yl]methyl}-1H-imidazo[4,5-c]quinoline as a white solid, mp 219.0-220.0° C.

Provenance & Evidence