Reacción #84334

Ecuación de reacción

N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

3,3-dimethyl-1-butyne

water

→

desired product

Rendimiento 99.7%

N-[2-[3-chloro-5-(3,3-dimethyl-1-butynyl)pyridin-2-yl]-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide

Rendimiento 99.7%

Disolventes

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of the reaction
2. 2
   Temperaturato cool to room temperature
3. 3
   Extracciónextracted with ethyl acetate (20 ml×1)
4. 4
   LavadoThe resulting organic layer was washed with water (10 ml×1)
5. 5
   Secadodried over saturated aqueous sodium chloride
6. 6
   Otroanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
7. 7
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

To a solution of 0.15 g of N-[2-(5-bromo-3-chloropyridin-2-yl)-2-(isopropoxyimino)ethyl]-2-(trifluoromethyl)benzamide and 0.05 g of 3,3-dimethyl-1-butyne in 3 ml of triethylamine, 0.04 g of copper(I) iodide and 0.02 g of dichlorobistriphenylphosphine palladium(II) were added, and the mixture was stirred at 80° C. for 3 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, mixed with 10 ml of water and extracted with ethyl acetate (20 ml×1). The resulting organic layer was washed with water (10 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 1:5 to 2:4) as the eluent to obtain 0.15 g of the desired product as a yellow resinous substance.

Fuente