Reacción #90815

Ecuación de reacción

2,5-dichloro-4-iodopyridine

2-amino-5-fluorobenzonitrile

potassium triphosphate

→

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

Rendimiento 86.0%

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 solvent was evaporated
4. 4
   workup.ADDITIONEther (50 ml) was added
5. 5
   Filtraciónthe solid was filtered

Procedimiento

To a degassed solution of 2,5-dichloro-4-iodopyridine (8 g, 29.2 mmol), 2-amino-5-fluorobenzonitrile (3.98 g, 29.2 mmol) and potassium triphosphate (18.60 g, 88 mmol) in 1,4-dioxane (100 ml) stirred under nitrogen at the room temperature was added DPEPhos (1.258 g, 2.337 mmol) and palladium acetate (0.262 g, 1.168 mmol). The reaction mixture was stirred at the reflux for 18 hr. The reaction mixture was filtered. The solvent was evaporated. Ether (50 ml) was added and the solid was filtered. 2-[(2,5-Dichloro-4-pyridinyl)amino]-5-fluorobenzonitrile (7.09 g, 25.1 mmol, 86% yield) was isolated as an orange solid. 1H NMR (400 MHz, METHANOL-d4) ppm 6.44 (s, 1 H) 7.46-7.58 (m, 2 H) 7.66 (dd, J=8.08, 2.78 Hz, 1 H) 8.08 (s, 1 H); HPLC Rt=3.23 min, MS (ESI): 382.0, 384.19 [M+H]+.

Fuente