Sodium Carbonate → HCID 86680613, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo picolinaldehyde (0.7 g, 3.76 mmol) in toluene (100 mL) and ethanol (75 mL) was added (4-carbamoylphenyl)boronic acid (1.24 g, 7.52 mmol), 2M sodium carbonate (2.8 g, 26.32 mmol, 6 mL water), Pd(PPh3)4 (0.217 g, 0.188 mmol) under argon. The resulting mixture was heated at 75-80° C., for 6 h. The contents were cooled to room temperature, diluted with ethyl acetate (150 mL) and washed with bicarbonate solution (2×100 mL) and brine solution (2×100 mL). The organic layer was dried over sodium sulphate and distilled off to obtain the crude product. The crude product was purified by flash chromatography (100-200μ; 35% ethyl acetate in hexane) to afford 4-(6-formylpyridin-3-yl)benzamide (0.53 g, 62% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.03 (s, 1H), 9.20 (s, 1H), 8.39 (d, 1H), 8.07 (s, 1H), 8.03 (d, 3H), 7.93 (d, 2H), 7.44 (s, 1H).

Provenance & Evidence