(Diethylamino)sulfur trifluoride → HCID 90203658, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-chloro-5-(3-hydroxyoxetan-3-yl)pyridine-2-carbonitrile (example 123b, 2.0 g, 9.5 mmol) in dry dichloromethane (50 ml) under an argon atmosphere cooled down to −75° C. was added DAST (1.61 g, 1.32 ml, 9.97 mmol). The reaction was stirred at −75° C. for 15 min, then let to warm up to 0° C. and stirred at 0° C. for 1 hour. The reaction was then quenched by addition of a 2M aqueous solution of sodium carbonate. The bi-phasic mixture was stirred at room temperature for 15 minutes, poured into a separatory funnel and extraction was carried out. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (1.81 g, 90%). MS (ESI, m/z): 213.0 (M+H+).

Provenance & Evidence