Water → benzyl 1H-indole-3-carboxylate

Participants

Reaction Steps

To a solution of 1H-indole-3-carboxylic acid (5 g, 31 mmol) in DMF (70 mL) under nitrogen atmosphere at 0° C. was added cesium carbonate (11 g, 31 mmol) and benzyl bromide (4.05 mL, 34.1 mmol). The reaction mixture was stirred at RT for 48 h and poured into water. EtOAc was added and the layers were separated, the aqueous one being back extracted three times with EtOAc. The combined organic layers were washed with water, dried over Na2SO4, filtered and concentrated. The residue was taken up in Et2O and the resulting precipitate was filtered-off to give the title compound. TLC, Rf (c-hexane/EtOAc 1:1)=0.55; MS (LC-MS): 252.1 [M+H]+, 274.0 [M+Na]+, 525.1 [2M+Na]+, 250.1 [M−H]−; tR (HPLC conditions a) 3.77 min.

Provenance & Evidence