Methyl Thioglycolate → HCID 58577947, compound

Temperature

90 °C

Potassium tert-butoxide (740.0 mg, 6.60 mmol) was added portionwise at room temperature to a solution of 5-bromo-2-fluoropyridine A-5 (0.31 mL, 3.00 mmol) and methyl 2-mercaptoacetate (0.55 mL, 6.00 mmol) in anhydrous 1-methylpyrrolidin-2-one (12.0 mL) under an argon atmosphere, in a 20 mL microwave reactor vial. The reaction mixture was sealed and heated at 90° C. for 3 mins under microwave irradiation, then successively cooled to room temperature, diluted with diethyl ether (150 mL), quenched with water (80 mL) and decanted. The aqueous layer was extracted with diethyl ether (2×150 mL); the combined extracts were sequentially washed with water (2×150 mL), brine (100 mL), dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient) to give methyl 2-(5-bromopyridin-2-ylthio)acetate A-13 (300.0 mg, Yield=39%). MS (ESI), [M+1]+ 262, 264.

1. customThe reaction mixture was sealed
2. temperaturesuccessively cooled to room temperature
3. customquenched with water (80 mL)
4. customdecanted
5. extractionThe aqueous layer was extracted with diethyl ether (2×150 mL)
6. washthe combined extracts were sequentially washed with water (2×150 mL), brine (100 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated to dryness under reduced pressure
10. customThe crude residue was purified by flash column chromatography on silica gel (hexanes:ethyl acetate gradient)

ORD record

ord-a697d8646990402ab65ff22484690156

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08637507B2