Citric Acid → HCID 57879442, compound

HRID 1673424Notes

Reaction equation

HRID 1673424 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1I.C(=O)([O-])[O-].[Cs+].[Cs+].[C:16]([NH:24][C:25]1[CH:37]=[C:36]([CH:38]=[CH2:39])[CH:35]=[CH:34][C:26]=1[C:27]([O:29]C(C)(C)C)=[O:28])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:16]([NH:24][C:25]1[CH:37]=[C:36](/[CH:38]=[CH:39]/[C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[F:1])[CH:35]=[CH:34][C:26]=1[C:27]([OH:29])=[O:28])(=[O:23])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 1375192,4-Difluoro-1-iodobenzeneHCID 67343635Tert-butyl 2-(benzamido)-4-vinylbenzoate

Product 1

HCID 57879442HCID 57879442, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

0.030 mL of 2,4-difluoroiodobenzene, 81 mg of cesium carbonate, 12 mg of tetrabutylammonium bromide and 19 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) were added to 1.0 mL of toluene solution containing 40 mg of tert-butyl 2-(benzamido)-4-vinylbenzoate at room temperature and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, 19 mg of polymer supported bis(acetato)triphenylphosphine palladium(II) was added and stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added. The organic layer was separated and dried over anhydrous magnesium sulfate after washed with 10% citric acid aqueous solution and a saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure. 10 mL of trifluoroacetic acid was added to the obtained residue and stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure and methanol was added to the obtained residue and a solid substance was separated by filtration to obtain 15 mg of 2-(benzamido)-4-((E)-2-(2,4-difluorophenyl)vinyl)benzoic acid as brown solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. additionwas added
  3. stirringstirred at 110° C. for 24 hours
  4. temperatureAfter the reaction mixture was cooled to room temperature
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter washed with 10% citric acid aqueous solution
  8. customa saturated sodium chloride aqueous solution sequentially, and the solvent was evaporated under reduced pressure
  9. addition10 mL of trifluoroacetic acid was added to the obtained residue
  10. stirringstirred at room temperature for 1 hour
  11. customThe solvent was evaporated under reduced pressure and methanol
  12. additionwas added to the obtained residue
  13. customa solid substance was separated by filtration

Sources & evidence

ORD record
ord-997d7404938445db9ab4f8818adcdaa2
Source dataset
uspto-grants-2011_08
Patent number
US07999132B2

Reaction notes

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