Reaction #90808

Reaction equation

2,5-dichloro-4-iodopyridine

2-amino-4-chlorobenzonitrile

potassium triphosphate

DPEPhos

→

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

Yield 57.1%

Solvents

1,4-dioxane

Conditions

Workup

1. 1
   Temperaturereflux for 18 hr
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   OtherThe solution was evaporated
4. 4
   workup.ADDITIONEther (50 ml) was added
5. 5
   Filtrationthe formed solid was filtered

Procedure

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]+.

Source