Sodium hydride → 3-(4-benzyloxyphenyl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine

Participants

Reaction Conditions

Reaction Steps

A suspension of 7-methyl-2-propylimidazo[4,5-b]pyridine (1.00 g, 5.71 mmol) and NaH (189 mg, 1.1 eq) in DMF (25 mL) was stirred for 1 hour and then cooled to 0° C. 4-Benzyloxybenzyl chloride (1.46 g; 1.1 eq) was then added and the ice bath removed. The reaction mixture was stirred for 2.5 hours and was then concentrated in vacuo. The residue was chromatographed on a silica gel flash chromatography column (30×200 mm) eluted with 30% ethyl acetate/hexane to yield 1.07 g (50%) of product.

Provenance & Evidence