4-Fluorobenzyl chloride → 8-(4-Fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine

Participants

Reaction Steps

To a stirred suspension under nitrogen of 15.0 g 8-hydroxy-2-methyl-imidazo[1,2-a]pyridine (from Step A) in 150 ml dimethylformamide maintained at 0°-5° C., was added 5.15 g 50% sodium hydride-oil dispersion in portions over 10 minutes. The mixturewas stirred in the cold 1/2 hr. and a brown solution resulted. 15.3 g 4-Fluorobenzyl chloride was added, and the solution was heated on a steam bath for 1/2 hr. The solution was poured into an ice bath and after 1/2 hour it became a brown solution. The solution was poured into 1.5 liters ice/water with vigorous stirring and the precipitate was separated by suction filtration, washed, and dried to give 8-(4-fluorobenzyloxy)-2-methylimidazo[1,2-a]pyridine (m.p. 137° C.).

Provenance & Evidence