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Water → HCID 136167052, compound

HRID 1617452
Notes
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Reaction equation

HRID 1617452 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]/[C:10](/[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[N:11]\[OH:12])=[CH:4][CH:3]=1.[CH3:25][S:26]([C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][CH:34]=1)(=[O:28])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>COCCOC>[CH3:25][S:26]([C:29]1[CH:34]=[C:33]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:9]/[C:10](/[C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:11]\[OH:12])=[CH:4][CH:3]=2)[CH:32]=[CH:31][CH:30]=1)(=[O:28])=[O:27]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27735423-(Methylsulfonyl)phenylboronic acidHCID 136167080HCID 136167080, compound

Product 1

HCID 136167052HCID 136167052, compoundYield 175.4%

Reagents, catalysts & solvents 1

HCID 8071
1,2-Dimethoxyethane
Solvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of (E)-3-(4-bromo-phenyl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (example 5, 10 mg), (3-methylsulfonylphenyl)boronic acid (58 mg), tetrakis-(triphenylphosphine)palladium (0) (30 mg) in 1,2-dimethoxyethane (2 mL) was added potassium carbonate (90 mg). The mixture was stirred at 80° C. overnight. Water was added, the phases were separated and the inorganic one was extracted with diethyl ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 2:1 to EtOAc) to yield (E)-3-(3′-methanesulfonyl-biphenyl-4-yl)-3-phenyl-1-pyridin-4-yl-propan-1-one oxime (21 mg, 18%) as a light yellow foam, MS (ESI+): m/z=457.2 ([M+H]+).

Workup

  1. customthe phases were separated
  2. extractionthe inorganic one was extracted with diethyl ether (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 2:1 to EtOAc)

Sources & evidence

ORD record
ord-2cfe0e183d364967b1781ed0ada05279
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765730B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes