반응 #518216

반응 방정식

water

2-ethynyl-6-methyl-pyridine

3-bromo-benzonitrile

triethylamine

→

title compound

수율 28.4%

3-[2-(6-Methylpyridin-2-yl)ethynyl]-benzonitrile

수율 28.4%

용매

dimethylformamide

반응 조건

후처리

1. 1
   온도The reaction mixture is cooled to ambient temperature
2. 2
   추출extracted with dichloromethane
3. 3
   건조The organic layer is dried over sodium sulfate
4. 4
   여과filtered
5. 5
   기타evaporated to dryness
6. 6
   기타the residue is purified by chromatography on silica gel with hexane/ethyl acetate (4:1) as eluant
7. 7
   기타Crystallization from hexane of the obtained product

실험 절차

A mixture of 1 g (8.54 mMol) 2-ethynyl-6-methyl-pyridine (prepared in analogy to D. E. Ames et al., Synthesis, 1981, p. 364-5), 2.3 g (12.8 mMol) 3-bromo-benzonitrile, 0.47 g (0.7 mMol) bis-(triphenylphosphine)-palladium-II-chloride, 80 mg (0.41 mMol) cuprous iodide and 1.53 ml (15 mMol) triethylamine in 10 ml dimethylformamide is stirred for 3 hours at 90° C. The reaction mixture is cooled to ambient temperature, poured into water and extracted with dichloromethane. The organic layer is dried over sodium sulfate, filtered, evaporated to dryness and the residue is purified by chromatography on silica gel with hexane/ethyl acetate (4:1) as eluant. Crystallization from hexane of the obtained product affords 0.53 g (28.4%) of the title compound as brown crystals, melting point 120-3° C.

출처