5-(3-Bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine → 6,2'-Difluoro-5'-[3-(2,4-difluorophenyl)-[1,2,4]triazin-5-yl]biphenyl-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a degassed mixture of 5-(3-bromo-4-fluorophenyl)-3-(2,4-difluorophenyl)-[1,2,4]triazine (0.2 g, 0.55 mmol) and 3-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (0.270 g, 1.1 mmol) in 1,4-dioxane (6 ml) and sodium carbonate (2 ml, 2N solution) was added tetrakis(triphenylphosphine)palladium(0), and the mixture heated at 80° C. Fog 24 h. The mixture was cooled to ambient temperature and partitioned between water (30 ml) and dichloromethane (40 ml). The aqueous layer was extracted with dichloromethane (2×40 ml) and the combined organics dried over Mg2SO4, filtered and the solvent removed at reduced pressure. The crude product was chromatographed on silica gel, eluent 5% ethyl acetate in dichloromethane, to give the product as a pale yellow solid (0.014 g): δH (400 MHz, CDCl3) 6.99-7.10 (2H, m), 7.49 (4H, m), 8.30-8.44 (3H, m), 9.69 (1H, dd, J 0.8, 2.0 Hz); m/z (ES+) 407.

Provenance & Evidence