Tris(1,1-dimethylethyl)phosphine → 3'-Amino-6,2',6'-trifluorobiphenyl-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-2,4-difluorophenylamine (0.6451 g, 3.10 mmol) and 3-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (0.915 g, 3.70 mmol) and potassium fluoride (0.5953 g, 10.2 mmol) in tetrahydrofuran (8 ml) was degassed with nitrogen for 15 min before adding tris(dibenzylideneacetone)dipalladium(0) (56.9 mg, 0.0621 mmol) and tri-tert-butylphosphine (1.24 ml of a 0.1 M solution in 1,4-dioxane, 0.124 mmol). The mixture was degassed for a further 5 min, then heated at 50° C. for 18 h under nitrogen. After cooling to ambient temperature, the mixture was partitioned between water (50 ml) and ethyl acetate (40 ml). The organic layer was washed with saturated aqueous NaCl (20 ml), dried (Na2SO4) and evaporated in vacuo. The residue was purified by chromatography (silica gel, 30% EtOAc/isohexane) to afford 0.5180 g (67%) of the title compound as a yellow solid: 1H NMR (360 MHz, CDCl3) δ 3.70 (2H, br s), 6.84–6.92 (2H, m), 7.44 (1H, t, J 8.4), 7.53 (1H, td, J 8.2, 5.1), 7.61 (1H, d, J 7.3).

Provenance & Evidence