Potassium Carbonate → Ethyl 5-acetoxy-N-(3,4-dichlorobenzyl)indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

3,4-Dichlorobenzyl bromide (5.96 g) was added to a stirred solution of ethyl 5-acetoxyindole-2-carboxylate (5.4 g) and potassium carbonate (6.94 g) in acetonitrile (500 ml) under an atmosphere of argon. The reaction was heated at 80° C. for 16 hours, then concentrated in vacuo and the residue partitioned between ethyl acetate and water. Combined organic extracts were washed with water, saturated aqueous sodium chloride and dried (MgSO4). The solvent was removed in vacuo and the residue was triturated with iso-hexane to give the product as a cream solid (5.55 g, 63%): NMR δ(CD3SOCD3) 1.27 (t, 3H), 2.27 (s, 3H), 4.28 (q, 2H), 5.82 (s, 2H), 6.90 (d, 1H), 7.09 (dd, 1H), 7.33-7.40 (m, 2H), 7.46 (d, 1H), 7.52 (d, 1H), 7.60 (d, 1H).

Provenance & Evidence