反応 #90770

反応方程式

N2

2,5-dichloro-4-iodopyridine

2-aminobenzonitrile

potassium triphosphate

DPEPhos

→

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

収率 79.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   温度at reflux for 18 hour
2. 2
   ろ過The solution was filtered through 0.5 in
3. 3
   その他The solution was evaporated
4. 4
   ろ過filtered
5. 5
   濃縮Diethyl ether was concentrated
6. 6
   ろ過the resulting solid was filtered

実験手順

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]+.

出典