Methylboronic Acid → 3-{4-[4-(4-Methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804175Notes

Reaction equation

HRID 1804175 reaction equation
Cl[C:2]1[CH:29]=[CH:28][C:5]([C:6]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:26][CH2:25][O:24][C:23]4=[O:27])=[CH:18][CH:17]=3)=[O:15])[CH2:10][CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:30]B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[F-].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.O1CCCC1>[CH3:30][C:2]1[CH:3]=[CH:4][C:5]([C:6]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:26][CH2:25][O:24][C:23]4=[O:27])=[CH:18][CH:17]=3)=[O:15])[CH2:12][CH2:13]2)=[O:7])=[CH:28][CH:29]=1

Participants

8

Reactant 4

HCID 139377Methylboronic AcidHCID 522689Potassium FluorideHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 673809143-{4-[4-(4-Chlorobenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one

Product 1

HCID 673808473-{4-[4-(4-Methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-oneYield 28.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3-{4-[4-(4-chlorobenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one (413 mg) described in Example 40, methylboronic acid (120 mg), palladium (II) acetate (11 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (41 mg) and potassium fluoride (232 mg) was added tetrahydrofuran (3 mL), and the mixture was refluxed for 5 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 (112 mg).

Workup

  1. temperaturethe mixture was refluxed for 5 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-c407703406ae45d199044f2f65f5cb32
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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