Sodium Carbonate → HCID 11195507, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-(5-bromopyridin-2-yl)ethanone (1.0 g, 5.0 mmol) in toluene (30 mL) and ethanol (20 mL) was added (4-methoxyphenyl)boronic acid (1.52 g, 10 mmol), 2M Na2CO3 (14 mL), Pd(PPh3)4 (0.057 g, 0.05 mmol), the reaction was purged with argon and heated at 80° C. for about 6 h. The reaction mixture was concentrated, diluted with water (100 mL), and extracted with ethyl acetate (2×300 mL). The combined organic extracts were washed with brine solution (20 mL), organic layer was dried over Na2SO4 and concentrated under vacuum to obtain crude product. The crude product was purified by flash chromatography (silica gel, 60-120μ) using 10% ethyl acetate in hexane eluent to afford 1-(5-(4-methoxyphenyl)-pyridin-2-yl)ethanone as off white solid (1 g, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.99 (s, 1H), 8.20 (d, 1H), 7.96 (d, 1H), 7.76 (d, 2H), 7.027 (d, 2H), 3.80 (s, 3H), 2.63 (s, 3H). LC-MS m/z calcd for [M+H]+ 228.09. found 228.2.

Provenance & Evidence