Cesium carbonate → HCID 68028001, compound

HRID 2406730Notes

Reaction equation

HRID 2406730 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].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.Cl[C:56]1[CH:61]=[CH:60][C:59]([N+:62]([O-:64])=[O:63])=[CH:58][N:57]=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>[N+:62]([C:59]1[CH:60]=[CH:61][C:56]([N:1]2[CH2:5][CH2:4][CH2:3][C:2]2=[O:6])=[N:57][CH:58]=1)([O-:64])=[O:63]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 120252-PyrrolidoneHCID 783082-Chloro-5-nitropyridineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 68028001HCID 68028001, compoundYield 99.9%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

Pyrrolidin-2-one (129 mg), cesium carbonate (412 mg), Pd2(dba)3 (116 mg), and Xantphos (146 mg) were added to a 1,4-dioxane (10 ml) solution containing 2-chloro-5-nitropyridine (200 mg) in a nitrogen atmosphere, followed by stirring at 100° C. for 5 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1), and a light red solid of 1-(5-nitropyridin-2-yl)pyrrolidin-2-one (261 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationSubsequently, the solvent was distilled away under reduced pressure
  5. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1)

Sources & evidence

ORD record
ord-c45df08ace64466e8adf00c08891efac
Source dataset
uspto-grants-2014_08
Patent number
US08809371B2

Reaction notes

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