Dichloromethane → N-benzyl-3-methyl-5-(2-oxo-4-phenethylpyridin-1(2H)-yl)thiophene-2-carboxamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-(5-(benzylcarbamoyl)-4-methylthiophen-2-yl)-2-oxo-1,2-dihydropyridin-4-yl trifluoromethanesulfonate (0.15 g, 0.32 mmol), phenethyl boronic acid (0.047 g, 0.31 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), 1:1 complex with dichloromethane (0.023 g, 0.028 mmol) and potassium carbonate (0.13 g, 0.95 mmol) in tetrahydrofuran (3 mL) and water (0.3 mL) was stirred in a sealed tube at 70° C. for 16 hours under nitrogen atmosphere. The reaction mixture was allowed to cool to ambient temperature, and was partitioned between ethyl acetate (75 mL) and water (35 mL). The organic layer was washed sequentially with 10% aqueous hydrochloric acid (30 mL), saturated aqueous sodium bicarbonate solution (2×25 mL) and brine (30 mL), then dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with 20% ethyl acetate in dichloromethane to afford the title compound as a light cream color solid in 40% yield (0.054 g): mp 145-146° C.; 1H NMR (300 MHz, CDCl3) δ 7.59 (d, J=7.3 Hz, 1H), 7.38-7.15 (m, 10H), 6.89 (s, 1H), 6.48 (s, 1H), 6.19 (t, J=5.8 Hz, 1H), 6.16 (dd, J=7.3, 1.9 Hz, 1H), 4.59 (d, J=5.8 Hz, 2H), 2.96-2.87 (m, 2H), 2.84-2.75 (m, 2H), 2.54 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.9, 160.7, 154.3, 140.1, 139.54, 139.5, 137.9, 133.2, 128.7, 128.6, 128.3, 127.8, 127.6, 127.2, 126.4, 121.8, 119.2, 109.3, 43.9, 36.9, 35.1, 15.9; MS (ES+) m/z 429.3 (M+1).

Provenance & Evidence