Potassium Carbonate → HCID 86760577, compound

Participants

Reaction Steps

The product of Step 2 (670 mg, 1.4 mmol), 4-pyridyl boronic acid (M. Lamothe et al J. Med. Chem., 1997, 40, 3542) (189 mg, 1.5 mmol), potassium carbonate (1.17 g, 8.5 mmol), triphenylphosphine (37 mg, 0.14 mmol), and palladium acetate (16 mg, 0.07 mmol) were dissolved in ethylene glycol dimethyl ether (15 ml) and water (5 ml). The biphasic solution was heated at reflux for 16 hours, with vigorous stirring, cooled, then filtered through a pad of celite, which was thoroughly washed with ethyl acetate. The two phase filtrate was separated and the organic phase washed with saturated sodium bicarbonate solution, water (×3) and brine. The solution was dried over magnesium sulfate and evaporated in vacuo to a crude solid (691 mg), which was purified by silica gel chromatography (1:9:90 0.880 ammonia:ethanol:dichloromethane), to afford the title product, (476 mg, 72%); MS (AP+) m/e 475 [M+H]+

Provenance & Evidence