Sodium Iodide → 8-(2,6-Dimethylbenzyloxy)-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine

Participants

Reaction Steps

A mixture of 8-hydroxy-3-hydroxymethyl-2-methylimidazo[1,2-a]pyridine (0.89 g, 5.0 mmol), sodium carbonate (1.5 g), sodium iodide (0.4 g), 2,6-dimethylbenzylchloride (0.7 g, 4.5 mmol) and acetone (60 ml) was stirred overnight. More sodium carbonate (1.0 g) was added. The reaction mixture was refluxed for 2 h. The reaction mixture was filtered and the solvent was removed in vacuo. The residue was suspended in CH2Cl2/MeOH (100:5) and filtered. Vacuum evaporation of solvent gave a residue which was purified by flash chromatography eluting with CH2Cl2—MeOH (100:4), collecting fractions, and recrystallized from CH2Cl2/CH3CN to give 0.37 g of the title compound.

Provenance & Evidence