Toluene → HCID 66604642, compound

Participants

Reaction Steps

To a suspension of crude 5-bromo-2-(3-((triisopropylsilyloxy)methyl)phenylamino)benzonitrile (3.9 g, 8.49 mmol), tetrakis(triphenylphosphine)palladium(0) (0.438 g, 0.379 mmol), toluene (60 mL), and 2 M aqueous sodium carbonate (9.63 mL, 19.27 mmol) under nitrogen were added a solution of 3,4-dichlorophenylboronic acid (2.203 g, 11.54 mmol) in MeOH (14 mL) at rt. The resulting reaction mixture was heated at reflux for 4 h. After cooling to room temperature, it was diluted with a mixture of water (150 mL) and EtOAc (250 mL) and the two phases were separated. The aqueous phase was extracted with ethyl acetate (2×100 mL), and the combined organic phases were washed with water (2×100 mL), 5% aqueous NH4OH solution (100 mL), and brine (100 mL). The organic phase was dried over Na2SO4 and the solvent removed. The crude material was purified by chromatography on silica gel, eluting with hexane containing 2%-5% EtOAc afforded 2.42 g of 3′,4′-dichloro-4-(3-((triisopropylsilyloxy)methyl)phenylamino)-biphenyl-3-carbonitrile. 1H NMR (CDCl3) δ ppm 7.65 (1H, d, J=1.83 Hz), 7.53-7.58 (2H, m), 7.39 (1H, dd, J=9.00, 2.29 Hz), 7.31 (1H, t, J=7.78 Hz), 7.22 (1H, s), 7.11 (1H, d, J=7.63 Hz), 7.07 (1H, d, J=8.85 Hz), 7.02 (2H, d, J=8.24 Hz), 6.35 (1H, s), 4.82 (2H, s), 1.13-1.22 (3H, m), 1.06-1.11 (18H, m).

Provenance & Evidence