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

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.

1. customThen the reaction mixture was degassed
2. customAfter one over night reaction mixture
3. stirringstirred under hydrogen atmosphere
4. additionAdditional catalyst (100 mg, 26% w/w) was added to the reaction mixture after 48 hours
5. stirringThe reaction mixture was stirred under hydrogen atmosphere for further 24 hours
6. filtrationfiltered through Celite®
7. customThe filtrate was evaporated to dryness under reduced pressure
8. customto obtain the crude product (320 mg)

ORD 기록

ord-70835d03fb2e48658f95876644e9abca

출처 데이터셋

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06232320B1