Реакция #90808

Уравнение реакции

2,5-dichloro-4-iodopyridine

2-amino-4-chlorobenzonitrile

potassium triphosphate

DPEPhos

→

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

Выход 57.1%

Растворители

1,4-dioxane

Условия реакции

Обработка

1. 1
   Температураreflux for 18 hr
2. 2
   ФильтрацияThe reaction mixture was filtered
3. 3
   ДругоеThe solution was evaporated
4. 4
   workup.ADDITIONEther (50 ml) was added
5. 5
   Фильтрацияthe formed solid was filtered

Методика

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]+.

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