반응 #157882

반응 방정식

6-[(E)-2-bromo-1-(4-tert-butylphenyl)ethenyl]-3-chloro-2-methoxypyridine

cesium carbonate

2-pyrrolidone

rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl

→

1-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

수율 75.0%

용매

toluene

Water

반응 조건

후처리

1. 1
   추출followed by extraction with ethyl acetate
2. 2
   세척The organic layer was washed with brine
3. 3
   건조dried over sodium sulfate
4. 4
   여과After filtration
5. 5
   기타the solvent was evaporated under reduced pressure
6. 6
   기타The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

실험 절차

A solution of 6-[(E)-2-bromo-1-(4-tert-butylphenyl)ethenyl]-3-chloro-2-methoxypyridine obtained in Reference Example 4-7 (109 mg), 2-pyrrolidone (73 mg), tris(dibenzylideneacetone)dipalladium(0) (11 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (22 mg) and cesium carbonate (329 mg) in toluene (3 mL) was stirred at an external temperature of 130° C. for four hours in a nitrogen atmosphere. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1) to give 1-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a yellow powder (82 mg, 75%).

출처