Cesium carbonate → HCID 19010505, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (294 mg, 0.902 mmol) was added to 2-methylimidazo[4,5-b]pyridine (60 mg, 0.451 mmol) in DMF (2 mL) at room temperature under nitrogen. After stirring at 50° C. for 15 min, a solution of 4-(1-carbomethoxy-1-(3,4-methylenedioxyphenyl)methoxy)-3,5-dipropylbenzyl bromide (from Step C) (27 1 mg, 0.585 mmol) in DMF (2 mL) was added and the mixture stirred at 50° C. for 12 h. After cooling to room temperature, the mixture was poured onto ice/water and extracted with ethyl acetate (4 times). The combined organic phase was washed with water twice, brine, dried (magnesium sulfate) and the solvent removed in vacuo. The crude product (a mixture of regioisomers) was purified by flash chromatography on silica-gel (3,4,5% methanol/methylene chloride) to provide the title compound (87 mg).

Provenance & Evidence