Cesium carbonate → HCID 58408403, compound

Participants

Reaction Steps

A solution of methyl 2-bromo-5-iodobenzoate (2-2, 2.0 g, 5.87 mmol, 1.0 equiv), 5-methylpyridine-3-boronic acid (0.803 g, 5.87 mmol, 1.0 equiv), Cs2CO3 (6.69 g, 20.53 mmol, 3.5 equiv) and PdCl2(dppf) (0.429 g, 0.587 mmol, 0.1 equiv) was made in DMF (30 mL) and stirred at room temperature overnight. The reaction mixture was partitioned between EtOAc and water. The layers were separated and the aqueous layer extracted with ethyl acetate. The combined organics were washed with saturated sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase column chromatography (25 to 75% EtOAc in hexanes) to afford the product (2-3) as a solid. ESI+ MS [M+H]+ C14H12BrNO2: 307.8 found, 307.1 required.

Provenance & Evidence