2,4-Dimethoxybenzylamine → HCID 89545592, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 6-bromoimidazo[1,2-a]pyridine-3-carboxylate (1.0 g, 3.7 mmol) in toluene (5 mL) was added 2,4-dimethoxybenzylamine (0.93 g, 5.6 mmol). The reaction mixture was heated at 120° C. for 2 days in a sealed tube, allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluting with a 0-100% gradient of ethyl acetate in hexanes to afford 6-bromo-N-(2,4-dimethoxybenzyl)imidazo[1,2-a]pyridine-3-carboxamide as a yellow oil in 20% yield (0.29 g): 1H NMR (300 MHz, CDCl3) δ9.70-9.67 (m, 1H), 7.91 (s, 1H), 7.53 (dd, J=9.5, 0.7 Hz, 1H), 7.38 (dd, J=9.5, 1.9 Hz, 1H), 7.27-7.21 (m, 2H), 6.48-6.38 (m, 2H), 4.54 (d, J=5.8 Hz, 2H), 3.85 (s, 3H), 3.78 (s, 3H); MS (ES+) m/z 389.8 (M+1), 391.8 (M+1).

Provenance & Evidence