Methanol → HCID 69811588, compound

Participants

Reaction Steps

To a solution of methyl 2-(4-cyanophenyl)-3-(2-oxoethyl)imidazo[1,2-a]pyridine-5-carboxylate in MeOH (0.2 M), 2,4-dimethoxybenzylamine (1.2 eq.) was added and the reaction mixture was stirred at RT for 2 h. Then, NaBH3CN (1.5 eq.) was added and stirring was continued for 12 h. The solvent was reduced in vacuo and the residue partitioned between sat. aq. NaHCO3 and DCM. The aqueous phase was separated and extracted several times with DCM. The combined organic extracts were washed with brine and dried (Na2SO4). Evaporation of the solvent gave a residue which was purified by flash column on silica using a gradient of EtOAc/Petroleum ether from 30:70 to 50:50 to yield (55% over two steps) the title compound. 1H NMR (600 MHz, DMSO-d6, 330K) δ 7.96 (2H, d, J=8.4 Hz), 7.93 (2H, d, J=8.4 Hz), 7.85 (1H, d, J=8.8 Hz), 7.80 (1H, d, J=7.0 Hz), 7.45 (1H; dd, J=9.0, 7.0 Hz), 7.22 (1H, d, J=8.0 Hz), 6.62 (1H, d, J=2 Hz), 6.53 (1H; dd, J=8.4, 2.0 Hz), 4.73 (2H; s), 3.84 (3H, s), 3.77 (3H, s), 3.72-3.68 (2H, m), 3.46-3.42 (2H, m). MS (ES+C26H22N4O3 requires: 438, found: 439 (M+H)+.

Provenance & Evidence