Cesium carbonate → Ethyl 4-[4-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]butanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-[3-(1H-indol-4-yl)-1,2,4-oxadiazol-5-yl]-2-[(1-methylethyl)oxy]benzonitrile (D49) (100 mg, 0.29 mmol), ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and cesium carbonate (189 mg, 0.58 mmol) in DMF (2 ml) was heated at 80° C. for 1 hour. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and heated overnight at 80° C. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and cesium carbonate (189 mg, 0.58 mmol) and heated for 24 hours. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and heated for 24 hours. Added ethyl 4-bromobutyrate (85 mg, 0.44 mmol) and heated for 6 hours. Added EtOAc (20 ml) and washed with water (20 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from ethanol to give the title compound (55 mg) as a white solid. MS (ES) C26H26N4O4 requires 458; found 459 (MH+).

Provenance & Evidence