Diethyl Ether → HCID 86680611, compound

Participants

Reaction Steps

To a solution of 4-(6-formylpyridin-3-yl)-N-methylbenzamide (0.2 g, 0.8 mmol) in THF (15 mL) at −30° C. was slowly added 3.0 M ethyl magnesium bromide in diethyl ether (0.9 mL, 2.4 mmol) and the reaction mixture was stirred at rt for 3 h. After completion of the reaction as monitored with TLC (5% MeOH\DCM), the reaction mixture was quenched with sat'd. NH4Cl (50 mL) solution. The reaction mixture was extracted with EtOAc (3×50 mL), washed with water (2×50 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (silica gel 230-400μ) using 2% methanol in dichloromethane. The product was isolated as a yellow solid (0.1 g, 45% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.82 (d, 1H), 8.46 (d, 1H), 8.11 (dd, 1H), 7.92 (d, 2H), 7.80 (d, 2H), 7.51 (d, 1H), 5.30 (d, 1H), 4.54 (q, 1H), 2.78 (d, 3H), 1.79 (m, 1H), 1.63 (m, 1H), 0.85 (t, 3H).

Provenance & Evidence