Cesium carbonate → HCID 23003167, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-hydroxyindole (5.0 g, 37.6 mmol) in dimethylformamide (200 mL) at room temperature was added cesium carbonate (18.4 g, 56.3 mmol). The reaction mixture was stirred at 60° C. for 30 min followed by the addition of 2,6-dichlorobenzyl bromide (9.0 g, 37.6 mmol). After stirring at 60° C. for 16 h, the reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and dried (Na2SO4). Purification by flash column chromatography (silica gel, hexane/ethyl acetate) yielded a clear oil (8.05 g, 73%). MS(ES) m/e 292.0 [M+H]+.

Provenance & Evidence