Sodium hydride → HCID 66803248, compound

Participants

Reaction Steps

To a solution of sodium hydride (60% dispersion in mineral oil, 90 mg, 2.25 mmol) in anhydrous THF (40 mL) at 0 C was added 2,2,2-trifluoro-ethanethiol (200 μL, 2.25 mmol) drop-wise under nitrogen. The resulting solution was stirred for 15 min and added to a solution of 6-chloro-nicotinic acid methyl ester (257 mg, 1.5 mmol) in anhydrous THF (40 mL) at 0 C drop-wise. The reaction mixture was allowed to warm to room temperature and stirring was continued for a further 3 h. The solution was quenched with water at 0 C and extracted into EtOAc (3×50 mL). Combined organics were washed with brine (20 mL), dried over magnesium sulfate, evaporated to dryness and purified by silica chromatography (25% EtOAc in heptane) to afford the title compound as a colourless oil (370 mg, 98%). Method C HPLC-MS: MH+ requires m/z=252. Found: m/z=252, Rt=1.41 min (94%).

Provenance & Evidence