(Diethylamino)sulfur trifluoride → HCID 178434334, compound

Participants

Reaction Conditions

Reaction Steps

2-Bromo-5-(difluoro(tetrahydro-2H-pyran-4-yl)methyl)-[1,2,4]triazolo[1,5-a]pyridine. (Diethylamino)sulfur trifluoride (4.26 mL, 32.2 mmol) was added to a stirred solution of (2-bromo-[1,2,4]triazolo[1,5-c]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (2 g, 6.45 mmol) in chloroform (40 mL) in a high pressure flask under nitrogen. The flask was sealed and heated at 50° C. for 16 h. The reaction was quenched with methanol (1 mL). The resulting mixture was diluted with ethyl acetate (200 mL) and washed with saturated aqueous sodium bicarbonate. The organics were washed with brine and then dried over magnesium sulfate, filtered, and concentrated on a rotary evaporator. The residue was purified using flash chromatography (5-50% ethyl acetate in hexane), to give the desired product (1.7 g, 5.12 mmol, 79% yield) as a light yellow solid. MS (ESI) m/z 334.2 [M+2]+.

Provenance & Evidence