Ammonium Chloride → HCID 90009117, compound

Participants

Reaction Conditions

Reaction Steps

1.0M Tetra-butyl ammonium fluoride in THF (13.23 mL, 13.23 mmol) was added to a THF solution (20 mL) of 1-(6-methoxypyridin-3-yl)ethanone (2 g, 13.23 mmol) and (trifluoromethyl)trimethylsilane (3.76 g, 26.5 mmol) under nitrogen at 0° C. The reaction was warmed to 25° C. and stirred for 18 hours, at which time LCMS showed >95% conversion to product. The reaction was diluted with 50 mL ethyl acetate and poured into 100 mL saturated NH4Cl; the organic layer was washed with 100 mL brine, dried over sodium sulfate, filtered and the filtrate concentrated. Silica gel chromatography using a linear gradient of 0-100% ethyl acetate/hexanes gave the title compound as a white solid. LCMS (M+H)+: 222.0. 1H NMR (500 MHz, CDCl3): δ 8.36 (d, J=1.9 Hz, 1H), 7.81 (dd, J=1.9 and 8.8 Hz, 1H), 6.79 (d, J=8.8 Hz, 1H), 3.97 (s, 3H), 2.80 (s, 1H), 1.80 (s, 3H).

Provenance & Evidence