Sodium Carbonate → HCID 86680607, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromopicolinaldehyde (1.0 g, 5.43 mmol) in toluene (10 mL) and ethanol (8 mL) was added (3-methoxyphenyl)boronic acid (1.2 g, 8.1 mmol), 2M sodium carbonate (3.4 g, 32.6 mmol, 8 mL water), Pd(PPh3)4 (0.228 g, 0.25 mmol) under argon. The resulting mixture was heated at 75-80° C., for 4 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, which was distilled off to obtain the crude product. The crude product was purified by flash chromatography (100-200 microns; 15% ethyl acetate in hexane) to afford 5-(3-methoxyphenyl)picolinaldehyde (0.75 g, 65% yield). 1H NMR (400 MHz, DMSO-d6): δ 10.02 (s, 1H), 9.14 (s, 1H), 8.33 (d, 1H), 7.98 (d, 1H), 7.45 (t, 1H), 7.38 (d, 2H), 7.03 (d, 1H), 3.84 (s, 3H); LC-MS m/z calculated for [M+H]+ 214.08 found, 214.3.

Provenance & Evidence