1,2-Dichloroethane → Ethyl 3-[3-chloro-5-(5-{3-chloro-4-[(trifluoromethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1H-indol-1-yl]propanoate

Participants

Reaction Conditions

Reaction Steps

3-Chloro-4-[(trifluoromethyl)oxy]benzoic acid (commercial: ABCR) (168 mg, 0.70 mmol) stirring in DMF (6 ml) was treated with EDC (146 mg, 0.76 mmol) followed by HOBt (104 mg, 0.76 mmol). The resultant solution was stirred for 15 minutes. Added ethyl 3-{3-chloro-5-[(hydroxyamino)(imino)methyl]-1H-indol-1-yl}propanoate (D96) (216 mg, 0.70 mmol) and stirred at RT for 45 minutes. The solution was heated at 80° C. for 6 hours then left standing at room temperature overnight. Single product formed by LC/MS. Added EtOAc (50 ml) and washed with water (50 ml), saturated aqueous sodium hydrogen carbonate (50 ml) and water (50 ml). Dried over MgSO4 and evaporated off the solvent. The residue was crystallised from ethanol to yield 200 mg of white solid. δH (400 MHz, d6-DMSO) 1.11 (3H, t), 2.92 (2H, t), 4.00 (2H, q), 4.49 (2H, t), 7.75 (1H, s), 7.80 (1H, d), 7.85 (1H, dd), 7.95 (1H, dd) 8.23 (1H, d) 8.30 (1H, dd), 8.47 (1H, d). MS (ES) C22H1635Cl37ClF3N3O4 requires 515; found 516 (MH+).

Provenance & Evidence