Cesium carbonate → (R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxooxazolidin-3-yl)phenyl}-4-methyloxazolidin-2-one

HRID 1804279Notes

Reaction equation

HRID 1804279 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[C:27]([CH3:28])=[CH:26][C:25]([CH3:29])=[CH:24][N:23]=3)[CH2:18][CH2:17]2)=[O:15])=[C:6]([N:8]2[CH2:12][CH2:11][O:10][C:9]2=[O:13])[CH:7]=1.[CH3:30][C@@H:31]1[CH2:35][O:34][C:33](=[O:36])[NH:32]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(P(C(C)(C)C)C1C(C)=C(C)C(C)=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>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.C1(C)C=CC=CC=1>[CH3:28][C:27]1[C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:14]([C:5]3[CH:4]=[CH:3][C:2]([N:32]4[C@H:31]([CH3:30])[CH2:35][O:34][C:33]4=[O:36])=[CH:7][C:6]=3[N:8]3[CH2:12][CH2:11][O:10][C:9]3=[O:13])=[O:15])[CH2:17][CH2:18]2)=[N:23][CH:24]=[C:25]([CH3:29])[CH:26]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 11953610Di-tert-butyl[3,4,5,6-tetramethyl-2',4',6'-tris(propan-2-yl)-[1,1'-biphenyl]-2-yl]phosphaneHCID 547552343-{5-Chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one

Product 1

HCID 58484689(R)-3-{4-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]-3-(2-oxooxazolidin-3-yl)phenyl}-4-methyloxazolidin-2-oneYield 40.8%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a mixture of 3-{5-chloro-2-[4-(3,5-dimethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one (207 mg) described in Preparation Example 120, (R)-4-methyloxazolidin-2-one (50.6 mg) described in Preparation Example 25, cesium carbonate (228 mg), tris(dibenzylideneacetone)dipalladium (0) chloroform (51.8 mg) and 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (24 mg) was added toluene (1 mL), and the mixture was refluxed for 8 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. After evaporation of the solvent, the residue was purified by column chromatography (ethyl acetate:methanol) to give the title compound (97.5 mg).

Workup

  1. temperaturethe mixture was refluxed for 8 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. customAfter evaporation of the solvent
  5. customthe residue was purified by column chromatography (ethyl acetate:methanol)

Sources & evidence

ORD record
ord-0f2902769d224430a57c6049c9f2f48a
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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