반응 #587908

반응 방정식

5-bromo-3-iodopyridin-2-amine

ethynyl-trimethyl-silane

EtOAc

→

5-bromo-3-(2-(trimethylsilyl)ethynyl)pyridin-2-amine

수율 55.6%

용매

Et3N

—

Petroleum ether

반응 조건

후처리

1. 1
   기타the resulting mixture was degassed with N2 for 2 minutes
2. 2
   기타the mixture was degassed again
3. 3
   기타The mixture was evaporated under reduced pressure
4. 4
   기타to give crude mixture which
5. 5
   기타was purified via a silica gel column
6. 6
   세척eluted with petroleum ether/EtOAc (20:1)

실험 절차

To a solution of 5-bromo-3-iodopyridin-2-amine (B-7-1) (20 g, 66.9 mmol) in Et3N (200 mL) was added CuI (1.27 g, 6.69 mmol), and the resulting mixture was degassed with N2 for 2 minutes. Then Pd(PPh3)2Cl2 (1.4 g, 20.1 mmol) was added and the mixture was degassed again. Then ethynyl-trimethyl-silane (7.2 g, 73.6 mmol) was added dropwise into the mixture at 0° C. The mixture was stirred at room temperature for 4 hours. TLC (Petroleum ether: EtOAc=5:1) showed that the reaction was complete. The mixture was evaporated under reduced pressure to give crude mixture which was purified via a silica gel column eluted with petroleum ether/EtOAc (20:1) to afford 5-bromo-3-(2-(trimethylsilyl)ethynyl)pyridin-2-amine (B-7-2) (10 g, 55.6%) as a white solid.

출처