Cesium carbonate → HCID 68961645, compound

HRID 2191715Notes

Reaction equation

HRID 2191715 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:62]1[CH:63]=[C:64]([OH:68])[CH:65]=[CH:66][CH:67]=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].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[OH:68][C:64]1[CH:63]=[C:62]([NH:1][C:2]2[CH:14]=[C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:12]=[CH:11][C:3]=2[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH:67]=[CH:66][CH:65]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 122723-IodophenolHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 58508425Tert-butyl 3-amino-[1,1'-biphenyl]-4-carboxylate

Product 1

HCID 68961645HCID 68961645, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-phenylbenzoate 0.20 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 17 mg, tris(dibenzylideneacetone)dipalladium(0) 7 mg, palladium acetate 2 mg and cesium carbonate 0.48 g was added 3-iodophenol 0.41 g, and it was heated and refluxed for 12 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 [Fuji SILYSIA Chemical Ltd., PSQ100B (spherical type), eluent; hexane:ethyl acetate=6:1] to give tert-butyl 2-((3-hydroxyphenyl)amino)-4-phenylbenzoate.

Workup

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

Sources & evidence

ORD record
ord-26e99f0561204b068dbe8c64482c2e2a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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