Water → 4-Benzenesulfonyl-6-(3'-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazin-2-one

HRID 560119Notes

Reaction equation

HRID 560119 reaction equation
[C:1]1([S:7]([N:10]2[CH2:15][CH:14]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18](Br)[CH:17]=3)[N:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:12](=[O:29])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:30][S:31]([C:34]1[CH:35]=[C:36](B(O)O)[CH:37]=[CH:38][CH:39]=1)(=[O:33])=[O:32].C(=O)([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:1]1([S:7]([N:10]2[CH2:15][CH:14]([C:16]3[CH:17]=[C:18]([C:38]4[CH:37]=[CH:36][CH:35]=[C:34]([S:31]([CH3:30])(=[O:33])=[O:32])[CH:39]=4)[CH:19]=[CH:20][CH:21]=3)[N:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:12](=[O:29])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 27735423-(Methylsulfonyl)phenylboronic acid2×HCID 670004364-Benzenesulfonyl-6-(3-bromo-phenyl)-1-phenyl-piperazin-2-one

Product 1

HCID 445485594-Benzenesulfonyl-6-(3'-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazin-2-oneYield 50%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-benzenesulfonyl-6-(3-bromo-phenyl)-1-phenyl-piperazin-2-one (100 mg), (3-methylsulfonylphenyl) boronic acid (46.7 mg) and tetrakis(triphenylphosphine)palladium(0) (24.5 mg) in 1,2-dimethoxyethane (2mL) was added potassium carbonate (73.3 mg). The reaction mixture was stirred at 80° C. overnight. Additional amounts of (3-methylsulfonylphenyl) boronic acid (21 mg), potassium carbonate (58.6 mg) and tetrakis(triphenylphosphine)palladium(0) (24.5 mg) were added and stirring was continued at 80° C. for 3 h. To the reaction mixture water and ethyl acetate were added, the phases were separated, and the inorganic one was extracted with ethyl acetate (×2). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude product was purified by column chromatography (SiO2, n-heptane/ethyl acetate 1:3, followed by ISOLUTE Flash NH2, n-heptane/ethyl acetate 1:1) to yield 58 mg (50%) of 4-benzenesulfonyl-6-(3′-methanesulfonyl-biphenyl-3-yl)-1-phenyl-piperazin-2-one as a white foam, MS: 547.3 (M+H)+.

Workup

  1. stirringstirring
  2. waitwas continued at 80° C. for 3 h
  3. customthe phases were separated
  4. extractionthe inorganic one was extracted with ethyl acetate (×2)
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chromatography (SiO2, n-heptane/ethyl acetate 1:3, followed by ISOLUTE Flash NH2, n-heptane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-b34ce2a156ba4ec9bc8548d1ddbc5a37
Source dataset
uspto-grants-2011_11
Patent number
US08063088B2

Reaction notes

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