Cesium carbonate → HCID 68962177, compound

HRID 2191717Notes

Reaction equation

HRID 2191717 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Br[C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[N:29]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH:28]=[CH:27]2.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>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.O.C1(C)C=CC=CC=1>[C:36]([O:35][C:33]([N:29]1[C:30]2[C:26](=[CH:25][C:24]([NH:1][C:2]3[CH:14]=[C:13]([CH2:15][CH2:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:32][CH:31]=2)[CH:27]=[CH:28]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 2728482N-Boc-5-bromoindoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl2×HCID 58508624Tert-butyl 2-amino-4-phenethylbenzoate

Product 1

HCID 68962177HCID 68962177, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalyst2×HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst2×HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To toluene 4.0 mL solution of tert-butyl 2-amino-4-phenethylbenzoate 0.20 g were added tert-butyl 5-bromo-1H-indol-1-carboxylate 0.29 g, cesium carbonate 0.55 g, tris(dibenzylideneacetone)dipalladium(0) 6 mg, palladium acetate 3 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 16 mg at room temperature, and it was heated and refluxed under nitrogen atmosphere for 8 hours. After the reaction mixture was cooled to room temperature, tris(dibenzylideneacetone)dipalladium(0) 6 mg, palladium acetate 3 mg and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 16 mg were added to it, and it was heated and refluxed under nitrogen atmosphere for 10 hours. After the reaction mixture was cooled to room temperature, water was added, and insoluble matter was filtrated. 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-((1-(tert-butoxycarbonyl)-1H-indol-5-yl)amino)-4-phenethylbenzoate.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 8 hours
  3. temperaturewas heated
  4. temperaturerefluxed under nitrogen atmosphere for 10 hours
  5. temperatureAfter the reaction mixture was cooled to room temperature
  6. filtrationinsoluble matter was filtrated
  7. customThe organic layer was separated
  8. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-576bdf3b16624ca597956eb078ac8c1a
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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