Reaktion #157861

Reaktionsgleichung

(5R)-5-[(Z)-2-bromo-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one

3,4-dichlorophenylboric acid

tri(2-furyl) phosphine

cesium carbonate

→

(5R)-5-[(E)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-(3,4-dichlorophenyl)ethenyl]pyrrolidin-2-one

Lösungsmittel

water

1,4-Dioxane

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationthe insoluble matter was filtered off through celite
2. 2
   Extraktionfollowed by extraction with ethyl acetate
3. 3
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   EinengenThe filtrate was concentrated under reduced pressure
6. 6
   SonstigeThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50→0:100)

Vorschrift

1,4-Dioxane (4 mL) and water (0.5 mL) were added to a mixture of (5R)-5-[(Z)-2-bromo-2-(5-cyclopropyl-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one (300 mg), 3,4-dichlorophenylboric acid (340 mg), tris(dibenzylideneacetone)dipalladium (81 mg), tri(2-furyl) phosphine (124 mg) and cesium carbonate (867 mg), and the mixture was stirred at 90° C. for three hours. Water and ethyl acetate were added to the reaction solution and the insoluble matter was filtered off through celite, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50→0:100) to give (5R)-5-[(E)-2-(5-cyclopropyl-6-methoxypyridin-2-yl)-2-(3,4-dichlorophenyl)ethenyl]pyrrolidin-2-one as a colorless amorphous (250 mg, 69%).

Quelle