Toluene → HCID 54754890, compound

HRID 1804162Notes

Reaction equation

HRID 1804162 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:24]2[CH2:28][CH2:27][O:26][C:25]2=[O:29])[CH:5]=[CH:6][C:7]=1[C:8]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=2[CH3:23])[CH2:12][CH2:11]1)=[O:9].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:38]1(B(O)O)[CH2:40][CH2:39]1.C1(C)C=CC=CC=1>C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1.[Cl-].[Cl-].[Pd+2].O>[CH:38]1([C:2]2[CH:3]=[C:4]([N:24]3[CH2:28][CH2:27][O:26][C:25]3=[O:29])[CH:5]=[CH:6][C:7]=2[C:8]([N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][C:17]=3[CH3:23])[CH2:14][CH2:15]2)=[O:9])[CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 1140TolueneHCID 62657Potassium Phosphate, TribasicHCID 2760897Cyclopropylboronic acidHCID 54754999HCID 54754999, compound

Product 1

HCID 54754890HCID 54754890, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 11556747Bis(tricyclohexylphosphine)palladium(II) DichlorideCatalystHCID 962WaterSolvent2×

Procedure

To a mixture of 3-{3-chloro-4-[4-(2,4-dimethylphenyl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one (347 mg) described in Example 21, bis(tricyclohexylphosphine)palladium (II) dichloride (33 mg), tripotassium phosphate (956 mg) and cyclopropylboronic acid (172 mg) were added toluene (4 mL) and water (200 μL), and the mixture was refluxed for 6 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (chloroform:methanol) to give the title compound (81 mg).

Workup

  1. temperaturethe mixture was refluxed for 6 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-37c94d5eadcb466fb3b2de03c7dcb600
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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