Cesium carbonate → HCID 66877664, compound

HRID 1015768Notes

Reaction equation

HRID 1015768 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

HCID 66877664HCID 66877664, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

(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.

Workup

  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)

Sources & evidence

ORD record
ord-48829f5ada1640ff9881b4000624126b
Source dataset
uspto-grants-2011_07
Patent number
US07985862B2

Reaction notes

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