Reacción #90770

Ecuación de reacción

N2

2,5-dichloro-4-iodopyridine

2-aminobenzonitrile

potassium triphosphate

DPEPhos

→

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

Rendimiento 79.0%

Disolventes

1,4-dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 18 hour
2. 2
   FiltraciónThe solution was filtered through 0.5 in
3. 3
   OtroThe solution was evaporated
4. 4
   Filtraciónfiltered
5. 5
   ConcentraciónDiethyl ether was concentrated
6. 6
   Filtraciónthe resulting solid was filtered

Procedimiento

The solution of 2,5-dichloro-4-iodopyridine (100 g, 365 mmol), 2-aminobenzonitrile (43.1 g, 365 mmol) and potassium triphosphate (233 g, 1095 mmol) in 1,4-dioxane (2.5 L) was degassed by N2 stream. To this solution was added DPEPhos (15.73 g, 29.2 mmol) and palladium acetate (3.28 g, 14.60 mmol). The reaction mixture was stirred at reflux for 18 hour. The solution was filtered through 0.5 in. celite and 0.2 inch of silica. The solution was evaporated. Solid was suspended in the diethyl ether and filtered. Diethyl ether was concentrated, and the resulting solid was filtered. 2-[(2,5-Dichloro-4-pyridinyl)amino]benzonitrile (80 g, 288 mmol, 79% yield) was isolated as an orange solid. 1H NMR (400 MHz, DMSO-d6) ppm 6.49 (s, 1 H) 7.50 (td, J=7.58, 1.01 Hz, 1 H) 7.56 (d, J=7.58 Hz, 1 H) 7.80 (td, J=7.83, 1.77 Hz, 1 H) 7.95 (dd, J=7.83, 1.52 Hz, 1 H) 8.26 (s, 1 H) 9.05 (brs, 1 H); HPLC Rt=2.88 min, MS (ESI): 263.9, 265.9 [M+H]+.

Fuente