3-Bromothieno[2,3-b]pyridine-2-carboxylic acid → {3-Bromothieno[2,3-b]pyridin-2-yl}methanol

A solution of 3-bromothieno[2,3-b]pyridine-2-carboxylic acid (14b) (30 mg, 0.12 mmol) in thionyl chloride (2 mL) was refluxed for 1 hour. All volatiles were removed by co-evaporation with toluene. The residue was diluted in dimethoxyethane (2 mL) and sodium tetraborohydride (5 mg, 0.13 mmol) was added to the solution at room temperature. The reaction mixture was stirred for 1 hour, then quenched with water (10 mL) 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 alcohol (14c) as a white solid without further purification (20 mg, 0.081 mmol, 68%).

1. customAll volatiles were removed by co-evaporation with toluene
2. additionThe residue was diluted in dimethoxyethane (2 mL)
3. customquenched with water (10 mL)
4. extractionextracted with ethyl acetate (2×10 mL)
5. washThe organic layer was washed with brine (10 mL)
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated under reduced pressure

ORD record

ord-3c4199ad94514c1389a1546ed0703174

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238026B2