Chloromethyl Methyl Ether → 1-methoxymethyl-1H-imidazo[4,5-b]pyridine

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Reaction Steps

4-Azabenzimidazole (7.5 g) was dissolved in DMF (125 mL), and cesium carbonate (68 g) was added thereto. Subsequently, chloromethyl methyl ether (7.0 mL) was added dropwise thereto under ice cooling, and the mixture was stirred for one hour at room temperature. Chloromethyl methyl ether (1.9 mL) was added to the reaction mixture, and the mixture was stirred for 12 hours at room temperature. A saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (0% to 15% methanol/chloroform), and the title compound (5.7 g) was obtained.

Provenance & Evidence