Trifluoroacetic acid → HCID 58459388, compound

Participants

Reaction Steps

2-((3-Bromo-8-chloroimidazo[1,2-a]pyridin-2-yl)methyl)isoindoline-1,3-dione was coupled with phenyl boronic acid according to Step C3b in General Procedure C. Partial hydrolysis of the phthalimide was observed under the reaction conditions. The crude intermediate was treated with DCM and TFA for a week. The reaction mixture was concentrated under reduced pressure and purified by reverse phase semi-prep HPLC. The fractions containing the desired product were lyophilized. The lyophilate was partitioned with satd. aq. NaHCO3 solution and EtOAc. The aq. layer was extracted three times with EtOAc. The combined organic layers were dried with Na2SO4, filtered, and concentrated under reduced pressure to give (8-chloro-3-phenylimidazo[1,2-a]pyridin-2-yl)methanamine.

Provenance & Evidence