Acrylamide → US9321721, Example 6

Beteiligte Stoffe

Reaktionsschritte

A mixture of acrylamide (6.2 mg, 0.087 mmol), 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-(4-iodophenyl)urea (9.2 mg, 0.022 mmol), and palladium(II) acetate (1.9 mg, 0.0087 mmol) in 0.6 mL degassed DMF:triethylamine (1:1) was reacted at 90° C. After 2.5 hours, the heating was stopped and the reaction stored at rt for 3 days in the dark. Then a catalytic amount of palladium(II) acetate was added and the heating resumed at 90° C. for 7.5 hours, then the temperature lowered to 65° C. for 16 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 chromatographed eluting with CHCl3/MeOH and then triturated with a CHCl3 plus 40% EtOAc/hexane mixture to give the title compound as a light tan solid (3.9 mg, 49%). 1H NMR (Acetone-d6) δ: 8.76-8.83 (m, 2H), 8.40 (d, J=2.6 Hz, 1H), 7.58-7.63 (m, 2H), 7.37-7.57 (m, 5H), 6.91 (br. s, 1H), 6.63 (d, J=15.8 Hz, 1H), 6.32 (br. s, 1H)

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