Reaktion #157882

Reaktionsgleichung

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

Ausbeute 75.0%

Lösungsmittel

toluene

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionfollowed by extraction with ethyl acetate
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over sodium sulfate
4. 4
   FiltrationAfter filtration
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→1:1)

Vorschrift

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%).

Quelle