Sodium Carbonate → Ethyl 3-(3-chloro-5-{5-[6-(methyloxy)-3-biphenylyl]-1,2,4-oxadiazol-3-yl}-1H-indol-1-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

Ethyl 3-(5-{5-[3-bromo-4-(methyloxy)phenyl]-1,2,4-oxadiazol-3-yl}-3-chloro-1H-indol-1-yl)propanoate (D106) (212 mg, 0.42 mmol), phenyl boronic acid (104 mg, 0.84 mmol), Pd(PPh3)4 (20 mg) and 2N aq. sodium carbonate solution (3 ml, 6 mmol) were suspended in DME (6 ml) and heated at 90° C. for 2 hours. Added phenyl boronic acid (30 mg, 0.24 mmol) and Pd(PPh3)4 (20 mg) and heated at 90° C. for a further 2 hours. Added EtOAc (70 ml) and washed with water (100 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from ethanol to yield the title compound as 90 mg of light tan solid. MS (ES) C28H2435ClN3O4 requires 501; found 502 (MH+).

Provenance & Evidence