Ethyl Acetate → 5-Bromo-3-[(trimethylsilyl)ethynyl]pyridin-2-amine

Participants

Reaction Steps

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.

Provenance & Evidence