[(S)-1-(3-Phenylaminopyridin-2-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester → [(S)-1-(1-Phenyl-1H-imidazo[4,5-b]pyridin-2-yl)ethyl]carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of [(S)-1-(3-phenylaminopyridin-2-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (980 mg, 2.75 mmol) in AcOH (25 mL) was heated for 10 h at 75° C. under a nitrogen atmosphere. The volatiles were removed in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was further extracted with DCM (×3) and the combined organic fractions washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo to afford the title compound as a light brown foam (920 mg, 99%). LCMS (Method C): RT 2.88 min [M+H]+ 339.3.

Provenance & Evidence