Ammonium Chloride → 1-(3-Phenyl-3H-imidazo[4,5-c]pyridin-2-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

LiHMDS (2.0M in THF/heptane/ethyl benzene, 3.9 mL, 7.79 mmol) was added to a stirred solution of 3-phenyl-3H-imidazo[4,5-c]pyridine (0.95 g, 4.87 mol) in THF (20 mL) at −78° C. under nitrogen. The resultant mixture was stirred at −78° C. for 10 minutes then at −10° C. for 15 minutes. The reaction mixture was re-cooled to −78° C. and N,N-dimethylacetamide (0.72 mL, 7.79 mmol) added then stirred at −78° C. for 5 minutes then at −10° C. for 15 minutes. The reaction mixture was poured into saturated aqueous ammonium chloride solution (30 mL) and extracted with EtOAc (3×30 mL). The combined EtOAc extracts were dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (SiO2 0-4% (2M ammonia in methanol) in DCM) to give the title compound as an off white solid (0.96 g, 76%) LCMS (method H): Rt 1.76 min, [M+H]+ 238

Provenance & Evidence