Citric Acid → HCID 67343568, compound

HRID 1673418Notes

Reaction equation

HRID 1673418 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.C(N(CCCC)CCCC)CCC.[C:26]([NH:34][C:35]1[CH:47]=[C:46]([CH:48]=[CH2:49])[CH:45]=[CH:44][C:36]=1[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C)C(=O)C>[C:26]([NH:34][C:35]1[CH:47]=[C:46](/[CH:48]=[CH:49]/[C:2]2[CH:7]=[CH:6][C:5]([O:8][C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=2)[CH:45]=[CH:44][C:36]=1[C:37]([O:39][C:40]([CH3:42])([CH3:43])[CH3:41])=[O:38])(=[O:33])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 7622Tributylamine2×HCID 5210081-Bromo-4-(trifluoromethoxy)benzene2×HCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 67343568HCID 67343568, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst2×HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

0.10 mL of 1-bromo-4-(trifluoromethoxy)benzene, 0.22 mL of tributylamine and 5.2 mg of palladium acetate were added to 2.0 mL of N,N-dimethylacetamide solution containing 0.15 g of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred under nitrogen atmosphere at 110° C. for 3 hours. After the reaction mixture was cooled to room temperature, 0.07 mL of 1-bromo-4-(trifluoromethoxy)benzene, 0.11 mL of tributylamine and 5.2 mg of palladium acetate were added at room temperature and stirred under nitrogen atmosphere at 110° C. for 2 hours. After the reaction mixture was cooled to room temperature, 10% citric acid aqueous solution and ethyl acetate were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution, a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. The obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; toluene; ethyl acetate=20:1] to obtain 0.10 g of tert-butyl 2-(benzamido)-4-((E)-2-(4-(trifluoromethoxy)phenyl)vinyl)benzoate as white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. stirringstirred under nitrogen atmosphere at 110° C. for 2 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. washafter washed with 10% citric acid aqueous solution
  7. customa saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified with silica gel column chromatography [PSQ100B (spherical) manufactured by Fuji Silysia chemical Ltd., eluent; toluene; ethyl acetate=20:1]

Sources & evidence

ORD record
ord-ed07c902d4b44637b23a489e18b0fbde
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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