Cesium carbonate → HCID 68961626, compound

HRID 2191707Notes

Reaction equation

HRID 2191707 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=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].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(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[NH:8]([C:9]1[CH:21]=[C:20]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:19]=[CH:18][C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 634876Binap, (A+-)-2×HCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 68961626HCID 68961626, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalyst2×HCID 1140TolueneSolvent

Procedure

Iodobenzene 0.10 mL was added to toluene 3.0 mL suspension of tert-butyl 2-amino-4-phenylbenzoate 0.10 g, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 2.3 mg, palladium acetate 0.8 mg and cesium carbonate 0.24 g, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 2.3 mg and palladium acetate 0.8 mg were added to it, and it was heated and refluxed for 24 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after washing with 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=20:1] to give tert-butyl 2-anilino-4-phenylbenzoate.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed for 24 hours
  3. temperaturewas heated
  4. temperaturerefluxed for 24 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. filtrationinsoluble matter was filtrated
  7. additionethyl acetate and 10% citric acid aqueous solution were added to it
  8. customThe organic layer was separated
  9. customcollected
  10. dry with materialdried over anhydrous magnesium sulfate
  11. washafter washing with saturated sodium chloride aqueous solution
  12. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b25f8b090e9048c9a3aba2320382e2d6
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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