3-Bromothieno[2,3-b]pyridine-2-carboxylic acid → {3-Bromothieno[2,3-b]pyridin-2-yl}methanol

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Reaction Steps

A solution of 3-bromothieno[2,3-b]pyridine-2-carboxylic acid (14b) (30 mg, 0.12 mmol) in thionyl chloride (2 mL) was refluxed for 1 hour. All volatiles were removed by co-evaporation with toluene. The residue was diluted in dimethoxyethane (2 mL) and sodium tetraborohydride (5 mg, 0.13 mmol) was added to the solution at room temperature. The reaction mixture was stirred for 1 hour, then quenched with water (10 mL) 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 alcohol (14c) as a white solid without further purification (20 mg, 0.081 mmol, 68%).

Provenance & Evidence