Sodium Carbonate → HCID 82078553, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(5-bromopyridin-2-yl)ethanone (1.0 g, 4.99 mmol) in toluene (100 mL) and ethanol (50 mL) was added 4-fluoro phenyl-boronic acid (1.4 g, 9.99 mmol), 2M sodium carbonate (3.7 g, 34.99 mmol, 12 mL water), Pd(PPh3)4 (0.228 g, 0.25 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 product was purified by flash chromatography (100-200μ; 35% ethyl acetate in hexane) to afford 1-(5-(4-fluorophenyl)pyridin-2-yl)ethanone (0.75 g, 66% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.12 (s, 1H), 8.25 (dd, 1H), 8.00 (d, 1H), 7.86 (m, 2H), 7.36 (t, 2H), 2.65 (s, 3H); LC-MS m/z calculated for [M+H]+ 216.23 found, 216.0.

Provenance & Evidence