Methyl 4-benzyloxythieno[2,3-c]pyridine-2-carboxylate → Methyl 4-hydroxythieno[2,3-c]pyridine-2-carboxylate

Participants

Reaction Steps

To a suspension of 10 wt % Pd on activated carbon (38 mg, 10% w/w) in absolute ethanol (3 mL) was added a cold solution of Example 236C (380 mg, 1.3 mmol) in ethanol (82 mL) under nitrogen atmosphere. Then the reaction mixture was degassed and stirred at room temperature under hydrogen atmosphere. After one over night reaction mixture was treated with additional 10 wt % Pd on activated carbon (190 mg, 50% w/w) and stirred under hydrogen atmosphere. Additional catalyst (100 mg, 26% w/w) was added to the reaction mixture after 48 hours. The reaction mixture was stirred under hydrogen atmosphere for further 24 hours and filtered through Celite®. The filtrate was evaporated to dryness under reduced pressure to obtain the crude product (320 mg). The title compound Example 236E was obtained in 75% yield (200 mg) by flash chromatography on silica gel eluting with 5% acetone-hexane followed by 40% acetone-hexane.

Provenance & Evidence