Ethyl Thioglycolate → Methyl 3-oxo-3,4-dihydro-2H-pyrido[3,2-b][1,4]thiazine-6-carboxylate

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 540 mg, 13.5 mmole) was added to a solution of ethyl thioglycolate (1.473 mL, 13.43 mmole) in DMF (48 mL) at 0° C. After 1 hr, methyl 6-amino-5-bromopyridine-2-carboxylate (3 g, 13 mmole; prepared by the method of Kelly, T. R.; Lang, F. J. Org. Chem. 1996, 61, 4623-4633) was added and the mixture was stirred at RT. After 16 hr, the solution was diluted with EtOAc (1 L), washed with water (3×300 mL), dried and concentrated to about 10 mL. The white solid was collected and washed with a little EtOAc to give the title compound (950 mg, 33%): MS (APCI−) m/e 223 (M−H)−.

Provenance & Evidence