Potassium Hydroxide → 3-Butyl-imidazo[1,5-a]pyridine-1-carboxylic acid

Participants

Reaction Steps

To a solution of 1-(3-butyl-imidazo[1,5-a]pyridin-1-yl)-2,2,2-trifluoro-ethanone (400 mg, 1.48 mmol) in EtOH (10 mL) was added KOH (830 mg, 14.8 mmol). The mixture was stirred at ambient temperature for 15 h. After this time the mixture was concentrated, diluted with water (10 mL) and acidified to pH 3 with 2N HCl. The aqueous mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to yield the title compound (200 mg, 62%). 1H NMR (DMSO-d6) δ 12.1 (1H), 8.38 (1H), 7.99 (1H), 7.18 (1H), 6.90 (1H), 2.99 (2H), 1.75 (2H), 1.38 (2H), 0.92 (3H); m/z (M+H)=219.0.

Provenance & Evidence