N-bromobutanimide → HCID 58459174, compound

Participants

Reaction Steps

Acetonitrile (8.5 ml) was added to 8-chloro-2-(chloromethyl)imidazo[1,2-a]-pyridine (341 mg, 1.7 mmol). N-bromosuccinimide (302 mg, 1.7 mL) was added and the mixture was stirred at rt until complete. The reaction mixture was partitioned with EtOAc and satd. aq. NaHCO3 solution. The organic layer was dried with Na2SO4, filtered, and concentrated under reduced pressure. The residue was taken up in DCM and purified by chromatography on a 23 g silica gel column using 0 to 70% gradient of EtOAc in hexane. The desired fractions were combined and concentrated under reduced pressure to give 3-bromo-8-chloro-2-(chloromethyl)imidazo[1,2-a]pyridine as a white crystalline solid.

Provenance & Evidence