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

HRID 20990

반응식

HRID 20990 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-9b5aef98020e4bc380e5b6f42844c23d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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