Toluene → HCID 66604928, compound

Participants

Reaction Steps

To a suspension of ethyl 4-(4-bromo-2-cyanophenylamino)benzoate (6.33 g, 18.34 mmol), tetrakis(triphenylphosphine)palladium(0) (0.438 g, 0.379 mmol), toluene (60 mL), and 2 M aqueous sodium carbonate (20.81 mL, 41.6 mmol) under nitrogen were added a solution of 3,4-dichlorophenylboronic acid (4.76 g, 24.94 mmol) in MeOH (18 mL) at rt. The resulting reaction mixture was heated at reflux temperature for 4 h. The reaction mixture was cooled to room temperature and diluted with water (100 mL) and ethyl acetate (250 mL). The aqueous phase was extracted with ethyl acetate (100 ml ×2), and the combined organic phase was washed with water (100 ml ×2), diluted (5%) aqueous ammonia (100 mL), and brine (100 mL). The organic phase was dried over Na2SO4, filtered, and concentrated. The crude material was suspended in dichloromethane and the solid was collected by filtration, and washed with DCM (5 ml ×2) to afford 5.33 g of ethyl 4-(3′,4′-dichloro-3-cyanobiphenyl-4-ylamino)benzoate. MS (ESI) m/z 411.0 (M+H). 1H NMR (CDCl3) δ ppm 8.04 (2H, d, J=8.55 Hz), 7.73 (1H, d, J=1.83 Hz), 7.58-7.66 (2H, m), 7.51 (1H, d, J=8.55 Hz), 7.46 (1H, d, J=8.85 Hz), 7.34 (1H, dd, J=8.24, 2.14 Hz), 7.20 (2H, d, J=8.55 Hz), 6.61 (1H, s), 4.37 (2H, q, J=7.12 Hz), 1.39 (3H, t, J=7.17 Hz).

Provenance & Evidence