Ammonia → 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone

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Reaction Steps

A mixture of 6-(1-ethoxyvinyl)-3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridine (440 mg, 1.42 mmol) in MeOH (2 mL) was added an aqueous solution of HCl (1N, 0.5 mL) and stirred at RT for 30 min. To the reaction mixture was added an aqueous ammonia solution (35%) until the pH was approximately 8. The aqueous solution was extracted with EtOAc (50 mL×3). The combined extracts were washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by SiO2 chromatography eluting with petroleum ether:EtOAc (1:1) to afford 300 mg (75%) of 1-(3-(4-methoxybenzyl)-3H-imidazo[4,5-c]pyridin-6-yl)ethanone as a white solid. MS (ESI): m/z=282.3 [M+1]+.

Provenance & Evidence