Reaktion #157840

Reaktionsgleichung

Phenylboronic acid

tri(2-furyl)phosphine

cesium carbonate

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

→

(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one

Lösungsmittel

1,4-dioxane

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITThe reaction solution was left
2. 2
   Temperaturto cool
3. 3
   Filtrationfiltered
4. 4
   WaschenThe filtrate was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   FiltrationAfter filtration
7. 7
   Sonstigethe solvent was evaporated under reduced pressure
8. 8
   SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:2)

Vorschrift

Phenylboronic acid (57 mg), tris(dibenzylideneacetone)dipalladium(0) (19 mg), tri(2-furyl)phosphine (32 mg) and cesium carbonate (151 mg) were added to a solution of (5R)-5-[(E)-2-(5-bromo-6-methoxypyridin-2-yl)-2-(4-tert-butylphenyl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-42 (80 mg) in 1,4-dioxane (1.5 mL)-water (0.5 mL), and the mixture was stirred at an external temperature of 65° C. for three hours. The reaction solution was left to cool, diluted with ethyl acetate and filtered. The filtrate 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→3:2) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(6-methoxy-5-phenylpyridin-2-yl)ethenyl]pyrrolidin-2-one as an orange oil (81 mg).

Quelle