Water → HCID 178436495, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-({3-[(3-bromo-5-chlorophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-2-ethyl-1H-imidazole-5-carboxamide (240 mg, 0.46 mmol), potassium vinyltrifluoroborate (122 mg, 0.92 mmol), PdCl2(dppf)-DCM (15 mg, 0.0184 mmol) and triethylamine (0.13 mL, 0.92 mmol) in n-PrOH (5 mL). The reaction was heated at 100° C. for 6 h, cooled to rt and water was added (20 mL). The aqueous mixture was extracted with EtOAc (3×20 mL) and the organic extracts were combined, dried over Na2SO4, filtered and concentrated. The crude material was purified by column chromatography (5% to 100% EtOAc/hexanes gradient) to afford the title compound (177 mg, 82%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 8.14 (br s, 1H), 7.47 (d, 1H), 7.35-7.30 (m, 2H), 7.01 (s, 1H), 6.81 (d, 1H), 6.72-6.64 (m, 2H), 5.92 (d, 1H), 5.35 (d, 1H), 4.51 (d, 2H), 2.58 (q, 2H), 1.16 (t, 3H).

Provenance & Evidence