Potassium Hydroxide → 3-Bromothieno[2,3-b]pyridine-2-carboxylic acid

Participants

Reaction Steps

A solution of ethyl 3-bromothieno[2,3-b]pyridine-2-carboxylate (14a) (50 mg, 0.17 mmol) and potassium hydroxide (96 mg, 1.7 mmol) in water (2 mL) and methanol (2 mL) was stirred at 80° C. for 1 hour. Water (10 mL) was added to the reaction mixture which was washed with diethyl ether (10 mL). The aqueous layer was acidified to pH 4 with a hydrochloric acid aqueous solution 1N and extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired acid (14b) as a white solid without further purification (30 mg, 0.12 mmol, 68%).

Provenance & Evidence