Methanol → Methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-hydroxyacetate

Participants

Reaction Steps

Acetyl chloride (725 μL, 10.2 mmol) was dropped at 0° C. in methanol (10 mL). After 30 minutes, a solution of 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-[(trimethylsilyl)oxy]acetonitrile (14e) (290 mg, 0.85 mmol) in methanol (5 mL) was added at 0° C. to the reaction. The mixture was then warmed at room temperature for 20 hours and concentrated in vacuo. A saturated aqueous solution of sodium bicarbonate (20 mL) was added to the residue and extracted with dichloromethane (2×20 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10) to afford the desired hydroxyl-ester (14f) as a white solid (180 mg, 0.6 mmol, 70%).

Provenance & Evidence