Chloroform → 2-(Chloromethyl)-3-propyl-3H-imidazo[4,5-b]pyridine

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Reaction Steps

2-aminopropyl-3-aminopyridine (172) (5.3 g, 35 mmol) is dissolved in 100 mL CHCl3 at room temperature. Ethyl chloromethylimidate hydrochloride (14 g, 89 mmol) is added followed by K2CO3 (25 g, 180 mmol). The suspension was stirred vigorously at room temperature for 3 hours. The reaction mixture is filtered through Celite and the solvent removed in vacuo. The residue is passed through a short plug of silica gel eluting with ethyl acetate to afford 3.7 g of 1-propyl-2-chloromethyl-7-azabenzimidazole (183). 1-propyl-2-(4-methoxybenzylamino)methyl-7-azabenzimidazole.

Provenance & Evidence