Cesium fluoride → HCID 11375606, compound

Participants

Reaction Steps

Charge a flask with trifluoromethanesulfonic acid 6-methoxy-1-[4-(2-piperidin-1-yl-ethoxy)-phenoxy]-naphthalen-2-yl ester (800 mg, 1.52 mmol), 3,4,5-trifluorobenzene boronic acid (804 mg, 4.57 mmol) and cesium fluoride (1.1 g, 7.6 mmol) and purge with nitrogen. In a separate flask, charge palladium(II)acetate (34 mg, 0.15 mmol) and tricyclohexylphosphine (64 mg, 0.23 mmol) and purge with nitrogen. Add degassed acetonitrile and sonicate under nitrogen for 10 minutes. Add the catalyst solution to the solids and plunge into an 80° C. oil bath for 10 minutes. Cool to room temperature and filter through celite. Concentrate and redissolve in methylene chloride. Wash with saturated aqueous sodium bicarbonate, separate, dry, filter and concentrate. Purify the residue over silica gel, eluting with 0 to 5% methanol in methylene chloride, to yield 720 mg (93%) of the title compound: mass spectrum (ion spray) 508.3 (M+H).

Provenance & Evidence