Water → tert-Butyl 5-(4-methylpiperazin-1-yl)-1H-indole-1-carboxylate

HRID 20990

Reaktionsgleichung

Reaktionsgleichung von HRID 20990
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+].O>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 161259585-Iodo-1H-indole, N-BOC protected

Produkt 1

HCID 58117405tert-Butyl 5-(4-methylpiperazin-1-yl)-1H-indole-1-carboxylateAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

1-(tert-Butoxycarbonyl)-5-iodoindole (3.46 g, 10.1 mmol) was dissolved in toluene (45.0 mL), and the solution was added with 4-methylpiperazine (2.24 mL, 20.2 mmol), 2,2′-(diphenylphosphino)-1,1′-binaphthyl (1.26 g, 2.02 mmol), cesium carbonate (4.94 mg, 15.2 mmol) and palladium acetate (226 mg, 1.01 mmol), followed by stirring under reflux for 24 hours. The mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (chloroform/methanol=9/1) to obtain 1-(tert-butoxycarbonyl)-5-(4-methylpiperazino)indole (887 mg, 28%).

Aufarbeitung

  1. temperatureunder reflux for 24 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography (chloroform/methanol=9/1)

Quellen und Nachweise

ORD-Eintrag
ord-9b5aef98020e4bc380e5b6f42844c23d
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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