Cesium carbonate → HCID 66798493, compound

Participants

Reaction Steps

A mixture of 2-(benzyloxy)-4-chloropyridine (800 mg, 3.653 mmol, 1.0 eq), benzyl methyl(piperidin-4-yl)carbamate (stage 3 AMN-52) (0.997 g, 4.018 mmol, 1.1 eq) and Cs2CO3 (2.374 g, 7.306 mmol, 2.0 eq) in toluene (10 ml) was degassed for 15 minutes with nitrogen. Pd2(dba)3 (166 mg, 0.182 mmol, 0.05 eq) and Xantphos (105 mg, 0.182 mmol, 0.05 eq) were then added and stirring was carried out for 14 hours at 90° C. After monitoring by TLC, the mixture was diluted with DCM (150 ml), washed with water (70 ml) and sat. NaCl solution (70 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 2.0% MeOH in DCM). Yield: 32% (500 mg, 1.160 mmol)

Provenance & Evidence