Ethyl Acetate → HCID 86617410, compound

HRID 2076639Notes

Reaction equation

HRID 2076639 reaction equation
C(=O)([O-])[O-:2].[Na+].[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][S:15]([NH:18][CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=1.CC1(C)C(C)(C)OB([C:28]2[CH:52]=[CH:51][C:31]([O:32][CH2:33][C:34]3[CH:46]=[CH:45][C:44]([C:47]([F:50])([F:49])[F:48])=[CH:43][C:35]=3[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[CH:30][CH:29]=2)O1.C(OCC)(=O)C>C1(C)C(CCO)=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[OH:2][C:43]1[C:44]([C:47]([F:48])([F:50])[F:49])=[CH:45][CH:46]=[C:34]([CH2:33][O:32][C:31]2[CH:51]=[CH:52][C:28]([C:8]3[CH:13]=[CH:12][C:11]([CH2:14][S:15]([NH:18][CH3:19])(=[O:17])=[O:16])=[CH:10][CH:9]=3)=[CH:29][CH:30]=2)[C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:40])[CH3:41])=[O:37]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 177413291-(4-Bromophenyl)-N-methylmethanesulfonamideHCID 67119026HCID 67119026, compound

Product 1

HCID 86617410HCID 86617410, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 882672-Methylphenethyl alcoholSolvent

Procedure

Tetrakis(triphenylphosphine)palladium (0) (10 mg, 8.9 μmol) and a 2N aqueous sodium carbonate solution (0.33 ml) were added to a solution of 1-(4-bromophenyl)-N-methylmethanesulfonamide (80 mg, 0.30 mmol) obtained in Example (29-1) and tert-butyl 2-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-5-(trifluoromethyl)benzoate (147 mg, 0.30 mmol) obtained in Example (22-4) in a mixture of toluene-ethanol (6:1, 1.2 ml), and the mixture was stirred with heating under reflux for 8 hours. Ethyl acetate and water were added to the reaction mixture and the insolubles were removed by filtration through Celite. After the obtained filtrate was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride/methanol=50/1) to give the title compound as a pale yellow powder (7 mg, yield: 4%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hours
  3. customthe insolubles were removed by filtration through Celite
  4. extractionAfter the obtained filtrate was extracted with ethyl acetate
  5. washthe organic layer was successively washed with water
  6. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  7. customThe residue obtained
  8. customby removing the solvent under reduced pressure
  9. customwas purified by silica gel preparative thin layer chromatography (developing solvent: methylene chloride/methanol=50/1)

Sources & evidence

ORD record
ord-0f4a94d788ba4b6bb1a54efa58808a5a
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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