Cesium carbonate → 3-[5-(5-{3-Chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]-2,2,3-trifluoropropanoic acid

Participants

Reaction Conditions

Reaction Steps

D5 (200 mg), Cs2CO3 (552 mg) and DMF (2.8 ml) were stirred at RT and treated with 3-bromo-2,2,3-trifluoropropanoic acid (175 mg). This mixture was heated at 140° C. for 1 hour in a microwave reactor. 2 further equivalents of Cs2CO3 (368 mg) were added and heating continued at 140° C. for 10 hours. The reaction mixture was then evaporated, treated with H2O, shaken and filtered to give a brown solid residue. This was purified by MDAP to give the title compound (12 mg) as a white solid. δH (methanol-d4, 400 MHz): 1.42 (6H, d), 4.83 (1H, septet), 6.87 (1H, d), 7.29 (1H, d), 7.45 (1H, d), 7.54 (1H, d), 7.61 (1H, d), 7.80 (1H, d), 8.06 (1H, d), 8.11 (1H, d), 8.19-8.22 (1H, m), 8.44 (1H, s).

Provenance & Evidence