Acetic Anhydride → 1-(4-methoxybenzyl)-6-bromo-1H-imidazo[4,5-c]pyridine

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Reaction Conditions

Reaction Steps

Acetic anhydride (1.28 mL, 13.6 mmol) was added to a solution of N4-(4-methoxybenzyl)-6-bromopyridine-3,4-diamine (1.05 g, 3.41 mmol) in triethylorthoformate (13 mL). The mixture was heated at 100° C. for 18 hours and then concentrated to give the title compound as a brown oil (1.18 g, quantitative). 1H NMR (d6-DMSO, 400 MHz) δ 8.75 (s, 1H), 8.60 (s, 1H), 8.00 (s, 1H), 7.35 (d, 2H, J=8.8 Hz), 6.90 (d, 2H, J=8.8 Hz), 5.45 (s, 2H), 3.70 (s, 3H). LCMS (2) Rt=2.27 min; m/z (ESI+) 318, 320 (MH+).

Provenance & Evidence