Ammonium Chloride → 1-(1-phenyl-1H-imidazo[4,5-c]pyridin-2-yl)ethanol

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Reaction Conditions

Reaction Steps

Methylmagnesium bromide (3.0M in diethyl ether, 2.1 mL, 6.36 mmol) was added to a stirred solution of 1-phenyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde (0.71 g, 3.18 mmol) in THF (25 mL) at −78° C. under nitrogen. The resulting mixture was stirred at −78° C. for 2 h then at −10° C. for 20 minutes, then re-cooled to −78° C. and additional methyl magnesium bromide (3.0M in diethyl ether, 1 mL, 3.00 mmol) added. The resultant mixture was stirred at −10° C. for 30 minutes then poured into saturated aqueous ammonium chloride solution (25 mL) and extracted with EtOAc (3×50 mL). The combined EtOAc extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was dissolved in THF (25 mL) and cooled to −78° C. and methyl magnesium bromide (3.0M in diethyl ether, 2.1 mL, 6.36 mmol) added, then stirred at −78° C. for 30 minutes followed by −10° C. for 1 h. The mixture was then poured into saturated aqueous ammonium chloride solution (25 mL) and extracted with EtOAc (3×50 mL). The combined EtOAc extracts were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by chromatography (SiO2 0-10% (2M ammonia in methanol) in DCM) to give the title compound as a yellow oil (0.36 g, 47%). LCMS (method H): Rt 1.42 min, [M+H]+ 240.

Provenance & Evidence