Triethylamine → HCID 90386939, compound

Participants

Reaction Steps

To a mixture of propynoic acid amide (41.4 mg, 0.60 mmol), 1-[2-fluoro-5-(trifluoromethyl)phenyl]-3-(3-iodophenyl)urea (169.7 mg, 0.40 mmol), triethylamine (0.167 mL, 1.2 mmol), dichlorobis(triphenylphosphine)palladium(II) (22.5 mg, 0.032 mmol), and triphenylphosphine (5.2 mg, 0.020 mmol) in 3.0 mL DMF (degassed) was added copper(I)iodide (7.6 mg, 0.04 mmol) and the reaction stirred at rt for 15 hours. The reaction was partitioned between EtOAc and H2O/brine mixture. The EtOAc layer was washed 3 times with H2O/brine mixture, then brine, dried with anhydrous Na2SO4 and rotary evaporated to a solid. The solid was triturated with hot MeOH and then triturated with hot EtOAc to give the title compound as a light tan solid (107.4 mg, 74%). 1H NMR (DSMO-d6) δ: 9.33 (s, 1H), 8.95 (d, J=2.1 Hz, 1H), 8.60 (dd, J=7.3, 2.1 Hz, 1H), 8.17 (br. s., 1H), 7.87 (s, 1H), 7.67 (br. s., 1H), 7.37-7.55 (m, 4H), 7.17-7.25 (m, 1H)

Provenance & Evidence