Reacción #90808

Ecuación de reacción

2,5-dichloro-4-iodopyridine

2-amino-4-chlorobenzonitrile

potassium triphosphate

DPEPhos

→

4-chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile

Rendimiento 57.1%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturareflux for 18 hr
2. 2
   FiltraciónThe reaction mixture was filtered
3. 3
   OtroThe solution was evaporated
4. 4
   workup.ADDITIONEther (50 ml) was added
5. 5
   Filtraciónthe formed solid was filtered

Procedimiento

To a degassed solution of 2,5-dichloro-4-iodopyridine (4.5 g, 16.43 mmol), 2-amino-4-chlorobenzonitrile (2.507 g, 16.43 mmol) and potassium triphosphate (10.46 g, 49.3 mmol) in 1,4-dioxane (60 ml) stirred under nitrogen at the room temperature was added DPEPhos (0.708 g, 1.314 mmol) and palladium acetate (0.148 g, 0.657 mmol). The reaction mixture was stirred at the reflux for 18 hr. The reaction mixture was filtered. The solution was evaporated. Ether (50 ml) was added and the formed solid was filtered. 4-chloro-2-[(2,5-dichloro-4-pyridinyl)amino]benzonitrile (2.8 g, 9.38 mmol, 57.1% yield) was isolated as an orange solid. 1H NMR (400 MHz, DMSO-d6) ppm 6.70 (s, 1 H) 7.53 (dd, J=8.34, 2.02 Hz, 1 H) 7.65 (d, J=2.02 Hz, 1 H) 7.95 (d, J=8.34 Hz, 1 H) 8.28 (s, 1 H) 9.12 (br. s., 1 H); HPLC Rt=3.50 min, MS (ESI): 298.0, 300.0 [M+H]+.

Fuente