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

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%).

1. concentrationconcentrated in vacuo
2. additionA saturated aqueous solution of sodium bicarbonate (20 mL) was added to the residue
3. extractionextracted with dichloromethane (2×20 mL)
4. washThe organic layer was washed with brine (10 mL)
5. dry with materialdried over sodium sulfate
6. filtrationfiltered
7. customevaporated under reduced pressure
8. customThe residue was purified by flash chromatography on silica gel (dichloromethane/ethyl acetate 90/10)

ORD record

ord-b8f51bcdf29c450399a2eb58034d0a6d

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238026B2