Hydrochloric Acid → HCID 68962151, compound

HRID 2191838Notes

Reaction equation

HRID 2191838 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:14][C:15]1[CH:27]=[C:26]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[CH:24][C:16]=1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(OCC)(=O)C.C1(C)C=CC=CC=1>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([NH:14][C:15]2[CH:27]=[C:26]([CH2:28][CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:25]=[CH:24][C:16]=2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:3][CH:4]=1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 71014-BromobiphenylHCID 10796Cesium carbonateHCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 68962151HCID 68962151, compoundYield 55.1%

Reagents, catalysts & solvents 5

HCID 167845palladium(II) acetateCatalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To toluene 1.0 mL solution of 4-bromobiphenyl 0.12 g were added 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 4.8 mg, tert-butyl 2-amino-4-phenethylbenzoate 60 mg, cesium carbonate 0.13 g, palladium acetate 0.50 mg and tris(dibenzylideneacetone)dipalladium(0) 1.8 mg at room temperature, and it was heated and refluxed for 5 hours and 30 minutes. 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 4.8 mg, palladium acetate 0.50 mg and tris(dibenzylideneacetone)dipalladium(0) 1.8 mg were added to it, and it was heated and refluxed for 7 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 1.0 mol/L hydrochloric acid 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=200:1] to give tert-butyl 2-((biphenyl-4-yl)amino)-4-phenethylbenzoate 50 mg of a yellow oil.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed for 5 hours and 30 minutes
  3. temperaturewas heated
  4. temperaturerefluxed for 7 hours
  5. customThe organic layer was separated
  6. washafter washing with saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-38a6f9da42d14ab28052057c37d77e9a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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