Methyl iodide → HCID 18617700, compound

Participants

Reaction Steps

A solution of 0.250 g (0.631 mmol) N-(2-[3-Cyano-indol-5-yl]ethyl)-4-(6-methoxypyrid-3-yl)benzamide (reference example 1p) in 5 mL DMF is added to a cooled (0° C.) solution of 0.0328 g (0.820 mmol) sodium hydride (60% dispersion in mineral oil) in 2 mL DMF. After ten minutes 0.043 mL (0.69 mmol) iodomethane is added, and the cooling bath removed. After 3 hours, the reaction is quenched with water, concentrated, and the resulting residue flash chromatographed (2:2:1 CH2Cl2:EtOAc:hexanes) to provide 0.167 g of the product as a white solid in 65% yield. 1H NMR (CDCl3) δ 3.09 (2H, t, J=7 Hz), 3.80 (2H, m), 3.86 (3H, s), 3.99 (3H, s), 6.17 (1H, m, br), 6.83 (1H, d, J=8 Hz), 7.29 (1H, s), 7.37 (1H, d, J=8 Hz), 7.55-7.58 (3H, m), 7.64 (1H, s), 7.76-7.82 (3 H, m), 8.40 (1H, d, J=2 Hz). MS (ion spray) m/z 411 (M+H)+.

Provenance & Evidence