Potassium Carbonate → HCID 69515307, compound

Participants

Reaction Steps

tert-Butyl 4,5-dibromo-2-furancarboxylate (H. Muratake et al, Chem. Pharm. Bull., 1997, 45, 799) (9.78 g, 30 mmol), 4-pyridyl boronic acid (M. Lamothe et al, J. Med. Chem., 1997, 40, 3542) (4.06 g, 33 mmol), potassium carbonate (24.8 g, 180 mmol), triphenylphosphine (786 mg, 3 mmol) and palladium (II) acetate (337 mg, 1.5 mmol) were dissolved in ethylene glycol dimethyl ether (150 ml) and water (75 ml). The mixture was heated at reflux for 18 hours with vigorous stiring, cooled then filtered through celite pad, which was thoroughly washed with ethyl acetate. The filtrate was then washed with saturated sodium bicarbonate solution, water (×3) and brine, then dried over magnesium sulfate. The solution was evaporated in vacuo and the residue purified by silica gel chromatography to afford the title product (5.32 g, 55%); MS (AP−) m/e 323/325 [M−H]−.

Provenance & Evidence