反応 #90808

反応方程式

2,5-dichloro-4-iodopyridine

2-amino-4-chlorobenzonitrile

potassium triphosphate

DPEPhos

→

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

収率 57.1%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度reflux for 18 hr
2. 2
   ろ過The reaction mixture was filtered
3. 3
   その他The solution was evaporated
4. 4
   workup.ADDITIONEther (50 ml) was added
5. 5
   ろ過the formed solid was filtered

実験手順

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]+.

出典