Acrylamide → HCID 78427113, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of acrylamide (24.7 mg, 0.347 mmol), 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-(3-iodophenyl)urea (36.8 mg, 0.087 mmol), and palladium(II) acetate (7.8 mg, 0.035 mmol) in 0.8 mL degassed DMF:triethylamine (1:1) was reacted at 75° C. After 14.5 hours a catalytic amount of palladium(II) acetate was added, the temperature increased to 85° C., and the reaction continued for an additional 3.5 hours. The reaction was partitioned between EtOAc and H2O/brine mixture. The EtOAc layer was washed with dilute aqueous HCl, then aqueous NaHCO3, brine, dried with anhydrous Na2SO4 and evaporated. The resulting solid was triturated with CHCl3/MeOH to give the title compound as a light tan solid (8.2 mg, 26%). 1H NMR (Acetone-d6) δ: 8.73-8.82 (m, 2H), 8.41 (br. s., 1H), 7.94 (s, 1H), 7.53 (d, J=15.7 Hz, 1H), 7.30-7.48 (m, 4H), 7.21-7.27 (m, 1H), 7.10 (br. s., 1H), 6.70 (d, J=15.7 Hz, 1H), 6.41 (br. s., 1H).

Provenance & Evidence