Toluene → HCID 68959360, compound

HRID 2191667Notes

Reaction equation

HRID 2191667 reaction equation
C1(C)C=CC=CC=1.[NH2:8][C:9]1[CH:21]=[C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:19]=[CH:18][C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[F:28][C:29]1[CH:34]=[CH:33][C:32](I)=[CH:31][CH:30]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.O>[F:28][C:29]1[CH:34]=[CH:33][C:32]([NH:8][C:9]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:19]=[CH:18][C:10]=2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:31][CH:30]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 96054-FluoroiodobenzeneHCID 10796Cesium carbonateHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 68959360HCID 68959360, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalyst2×HCID 634876Binap, (A+-)-Catalyst2×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To toluene 7.5 mL solution of tert-butyl 2-amino-4-phenylbenzoate 0.50 g were added 1-fluoro-4-iodobenzene 0.22 mL, cesium carbonate 1.3 g, palladium acetate 4.3 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 12 mg at room temperature, and it was heated and refluxed for 4 hours. After the reaction mixture was cooled to room temperature, palladium acetate 4.3 mg and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 12 mg were added to it, and it was heated and refluxed for 13 hours. After the reaction mixture was cooled to room temperature, water and ethyl acetate were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-(4-fluoroanilino)-4-phenylbenzoate 0.44 g of brown oil.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 4 hours
  3. temperaturewas heated
  4. temperaturerefluxed for 13 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. customThe organic layer was separated
  7. customcollected
  8. dry with materialdried over anhydrous magnesium sulfate
  9. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  10. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-043553d44625434ab40548514033acbb
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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