Indole → HCID 3399806, compound

Participants

Reaction Steps

A solution of indole (5.6 g 48 mmol,) in DMF at 0° C. was treated with sodium hydride (1.84 g, 48 mmol), stirred for 10 minutes at room temperature, treated with methyl 4-(bromomethyl)benzoate (10 g, 44 mmol) and stirred at room temperature overnight. The reaction mixture was diluted with EtOAc, washed with saturated NaHCO3, dried over MgSO4 and concentrated in vacuo to give a solid residue. The resultant residue was purified by column chromatography (silica, EtOAc:hexanes, 30%) to give the title product in 91% yield, identified by NMR and mass spectral analyses. LCMS (ESI+) 266 (MH+).

Provenance & Evidence