Potassium Hydroxide → 3-Bromothieno[2,3-b]pyridine-2-carboxylic acid

A solution of ethyl 3-bromothieno[2,3-b]pyridine-2-carboxylate (14a) (50 mg, 0.17 mmol) and potassium hydroxide (96 mg, 1.7 mmol) in water (2 mL) and methanol (2 mL) was stirred at 80° C. for 1 hour. Water (10 mL) was added to the reaction mixture which was washed with diethyl ether (10 mL). The aqueous layer was acidified to pH 4 with a hydrochloric acid aqueous solution 1N and extracted with ethyl acetate (2×10 mL). The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to afford the desired acid (14b) as a white solid without further purification (30 mg, 0.12 mmol, 68%).

1. washwas washed with diethyl ether (10 mL)
2. extractionextracted with ethyl acetate (2×10 mL)
3. washThe organic layer was washed with brine (10 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure

ORD record

ord-866893295f8b43bf953f7f9b7c6133ed

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238026B2