Potassium vinyltrifluoroborate → HCID 178436594, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-({3-[(3-bromo-5-cyanophenyl)oxy]-4-chloro-2-fluorophenyl}methyl)-4-chloro-2-methyl-1H-imidazole-5-carboxamide (0.480 g, 0.964 mmol), potassium vinyltrifluoroborate (0.194 g, 1.445 mmol) and 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane complex (0.079 g, 0.096 mmol) in n-propanol (8 ml) was added TEA (0.672 ml, 4.82 mmol) and the reaction mixture was heated at 100° C. for 4 hours. The reaction mixture was diluted with EtOAc and washed with water. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-chloro-N-({4-chloro-3-[(3-cyano-5-ethenylphenyl)oxy]-2-fluorophenyl}methyl)-2-methyl-1H-imidazol e-5-carboxamide (0.263 g, 0.591 mmol, 61% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.05 (t, 1H), 7.77 (s, 1H), 7.47 (d, 1H), 7.40 (br. s., 1H), 7.32 (t, 1H), 7.26 (br. s., 1H), 6.72 (dd, 1H), 6.01 (d, 1H), 5.41 (d, 1H), 4.51 (d, 2H), 2.23 (s, 3H).

Provenance & Evidence