Methyl Thioglycolate → HCID 58577947, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence