Methyl iodide → Ammonium Hydroxide

Participants

Reaction Steps

7-Methyl-3H-imidazo[4,5-b]pyridine (2.0 g, 15 mmol) was dissolved in acetone (60 ml) and treated with freshly ground KOH (4.21 g) followed by dropwise addition of iodomethane (10 ml). After 10 min, the reaction mixture was poured into satd. aq. NaHCO3 (25 ml) in water (25 ml) and extracted with DCM (4×80 ml). The organic layers were combined and dried over Na2SO4, filtered, and concentrated. SGC (DCM:MeOH:NH4OH =96:4:1 as eluant) yielded 3,7-dimethyl-3H-imidazo[4,5-b]pyridine (1.05 g). 1H NMR (CDCl3) δ 7.94 (s, 1H), 7.83 (d, 1H), 6.48 (s, 1H), 3.04 (s, 3H), 2.07 (s, 3H).

Provenance & Evidence