Cesium carbonate → tert-butyl 2-(1-benzyl-2-ethyl-1H-indol-4-yloxy)acetate

Participants

Reaction Conditions

Reaction Steps

2-Ethyl-4-hydroxy-1-(phenylmethyl)-1H-indole (5.82 g, 20 mmol) was added to 7.82 g (24 mmol) cesium carbonate in 25 mL DMF and the mixture stirred at 35° C. for 30 minutes. After cooling to 20° C., a solution of tert-butyl bromoacetate (4.65 g, 23.8 mmol) in 5 mL DMF was added and stirring maintained until the reaction was judged complete by TLC analysis (several hours). The mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate solution was washed with brine, dried (MgSO4) and concentrated at reduced pressure to give 6.8 g of solid. Mass spectrum: 365

Provenance & Evidence