Perchloric Acid → Methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-(tert-butoxy)acetate

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Reaction Steps

Under a nitrogen atmosphere, perchloric acid (70%, 750 μL) was added at −10° C. to a solution of methyl 2-{3-bromothieno[2,3-b]pyridin-2-yl}-2-hydroxyacetate (14f) (180 mg, 0.6 mmol) in tertbutyl acetate (5 mL). After 1 hour, the reaction was quenched with a saturated aqueous solution of sodium bicarbonate and extracted with dichloromethane (2×10 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 product (14g) as a white solid (55 mg, 0.15 mmol, 26%).

Provenance & Evidence