Cesium carbonate → 1-(5-Bromo-3-pyridinyl)-2-pyrrolidinone

HRID 2406703Notes

Reaction equation

HRID 2406703 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Br:55][C:56]1[CH:57]=[N:58][CH:59]=[C:60](Br)[CH:61]=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[Br:55][C:56]1[CH:61]=[C:60]([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH:59]=[N:58][CH:57]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 693693,5-DibromopyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 686194601-(5-Bromo-3-pyridinyl)-2-pyrrolidinoneYield 44.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Cesium carbonate (213 mg), pyrrolidin-2-one (45 mg), Xantphos (76 mg), and Pd2(dba)3 (60 mg) were added to a 1,4-dioxane (4 ml) solution containing 3,5-dibromopyridine (100 mg) in a nitrogen atmosphere, followed by reflux for 4 hours. The reaction mixture was adjusted to room temperature and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 1:1), and a white solid of 1-(5-bromopyridin-3-yl)pyrrolidin-2-one (45 mg) was thus obtained.

Workup

  1. temperatureby reflux for 4 hours
  2. customwas adjusted to room temperature
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe resultant was washed with saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThen, the solvent was distilled away under reduced pressure
  7. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=3:1 to 1:1)

Sources & evidence

ORD record
ord-70505be4295044a795d0ca022ef5db94
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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