Cesium carbonate → HCID 66877664, Verbindung

HRID 1015768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1015768
Br[C:2]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:3]=1[C:4]#[N:5].[NH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:10][C:7]1[CH:8]=[CH:9][C:2]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])=[C:3]([CH:6]=1)[C:4]#[N:5]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 103309442-Bromo-5-chlorobenzonitrile

Produkt 1

HCID 66877664HCID 66877664, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

(Step 1) To a solution (139 ml) of 2-bromo-5-chlorobenzonitrile (15.0 g), pyrrolidin-2-one (7.90 ml) and cesium carbonate (45.2 g) in 1,4-dioxane were added tris(dibenzylideneacetone)dipalladium (1.59 g) and 4,5-bis(biphenylphosphino)-9,9-dimethylxanthine (2.0 g) at room temperature under a nitrogen atmosphere, and the mixture was heated under reflux for 3 hr. The mixture was allowed to cool to room temperature, and extracted with ethyl acetate and water. The organic layer was filtered through celite, and washed with ethyl acetate. The filtrate was dried over sodium sulfate, and filtered. The solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (ethyl acetate:hexane=1:10→1:1) to give 5-chloro-2-(2-oxopyrrolidin-1-yl)benzonitrile (12.5 g) as yellow crystals.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. extractionextracted with ethyl acetate and water
  4. filtrationThe organic layer was filtered through celite
  5. washwashed with ethyl acetate
  6. dry with materialThe filtrate was dried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by column chromatography (ethyl acetate:hexane=1:10→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-48829f5ada1640ff9881b4000624126b
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985862B2

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