Formic Acid → HCID 90386929, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-{3-[({[2-fluoro-5-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenyl}prop-2-ynamide (31.0 mg, 0.085 mmol), iodobenzene (0.010 mL, 0.089 mmol), diethylamine (0.029 mL, 0.281 mmol), formic acid (0.0083 mL, 0.221 mmol), and bis(dibenzylideneacetone)palladium(0) (3.4 mg, 0.006 mmol) in 1.1 mL EtOAc (degassed) was heated at 75° C. for 16 hours. The reaction was partitioned between EtOAc and H2O/brine mixture. The EtOAc layer was washed with H2O/brine mixture, brine, dried with anhydrous Na2SO4 and rotary evaporated. The crude material was chromatographed eluting with EtOAc/CHCl3 to give the higher Rf material as an off-white solid. The solid was recrystallized from EtOAc/hexane to give the title compound as a white solid (7.5 mg, 20%). 1H NMR (CD3CN) δ: 8.54-8.58 (m, 1H), 7.89 (s, 1H), 7.71 (d, J=3.2 Hz, 1H), 7.14-7.39 (m, 10H), 6.78-6.82 (m, 1H), 6.39 (s, 1H), 6.14 (br. s, 1H), 5.79 (br. s, 1H).

Provenance & Evidence