Reaktion #157816

Reaktionsgleichung

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

cesium carbonate

4-tert-butylphenylboronic acid

tri(2-furyl)phosphine

→

(5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)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=90:10→60:40)

Vorschrift

1,4-Dioxane (8 mL) and water (2 mL) were added to a mixture of (5R)-5-[(Z)-2-bromo-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one obtained in Reference Example 4-18 (531 mg), 4-tert-butylphenylboronic acid (570 mg), tris(dibenzylideneacetone)dipalladium (147 mg), tri(2-furyl)phosphine (224 mg) and cesium carbonate (1.04 g), and the mixture was stirred at 90° C. for 2.5 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=90:10→60:40) to give (5R)-5-[(E)-2-(4-tert-butylphenyl)-2-(5-chloro-6-methoxypyridin-2-yl)ethenyl]pyrrolidin-2-one as a pale yellow amorphous (597 mg).

Quelle