반응 #69109

반응 방정식

3-Iodo-5-trifluoromethylpyridin-2-amine

TMS acetylene

→

product

수율 101.8%

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

수율 101.8%

용매

THF

ethyl acetate

반응 조건

후처리

1. 1
   기타the reaction mixture degassed under nitrogen
2. 2
   온도The reaction mixture was cooled in an ice bath
3. 3
   workup.ADDITIONUpon complete addition the reaction
4. 4
   여과filtered through silica
5. 5
   세척washed through with 4×150 mL ethyl acetate
6. 6
   농축The filtrates were concentrated
7. 7
   기타the solid was triturated from heptane (250 mL)

실험 절차

To a stirred solution of 3-Iodo-5-trifluoromethylpyridin-2-amine (61.38 g, 213 mmol) in anhydrous THF (200 mL) under a nitrogen atmosphere was added Pd(PPh)3Cl2 (1.5 g, 2.1 mmol), and copper iodide (0.406 g, 2.1 mmol) and the reaction mixture degassed under nitrogen. The reaction mixture was cooled in an ice bath and TMS acetylene (36 mL, 256 mmol) was added dropwise over 30 minutes. Upon complete addition the reaction was allowed to warm to room temperature and monitored until the reaction was complete. The mixture was diluted with ethyl acetate (200 mL) and filtered through silica washed through with 4×150 mL ethyl acetate. The filtrates were concentrated and the solid was triturated from heptane (250 mL) to give 56 g of product.

출처