Potassium Carbonate → HCID 66696613, compound

Participants

Reaction Steps

6-(trifluoromethyl)nicotinaldehyde (7 g, 40 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (8.41 g, 40.0 mmol) and K2CO3 (6.63 g, 48.0 mmol) were heated to reflux in methanol (200 mL) overnight. The solution was cooled and the solvents removed in vacuo. The orange semi-solid was partitioned between water and ethyl acetate. The organic phase was washed with water and brine, dried over Na2SO4, filtered, and the solvents removed in vacuo. The crude product was purified by column chromatography with 10% to 45% ethyl acetate/hexanes as eluent to afford 8.06 g (88% yield) of the title compound as a yellow solid. 1H NMR (300 MHz, CDCl3): δ 9.01 (d, J=2.03 Hz, 1H), 8.08 (dd, J=7.97, 1.86 Hz, 1H), 7.93 (s, 1H), 7.77 (d, J=8.48 Hz, 1H), 2.51 (s, 3H,). MS (ESI+) m/z 229 (M+H)+.

Provenance & Evidence