Ethyl Acetate → 3-[2-(t-Butyloxycarbonylamino)ethyl]-5-(4-bromo-1-methylpentyloxy)-1H-indol

HRID 2256393

반응식

HRID 2256393 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([OH:20])[CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:21][CH:22]([CH2:24][CH2:25][CH:26](Br)[CH3:27])[CH3:23].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>C(#N)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH:26]([CH3:27])[CH2:25][CH2:24][CH:22]([Br:21])[CH3:23])[CH:18]=2)[NH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 912322,5-DibromohexaneHCID 10401227tert-butyl 2-(5-hydroxy-1H-indol-3-yl)ethylcarbamate

생성물 1

HCID 190299193-[2-(t-Butyloxycarbonylamino)ethyl]-5-(4-bromo-1-methylpentyloxy)-1H-indol수율 30.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 3-[2-(t-butyloxycarbonylamino)ethyl]-5-hydroxy-1H-indole (1.34 g, 4.86 mmol) in acetonitrile (50 mL) were added 2,5-dibromohexane (2.4 g, 9.72 mmol) and potassium carbonate (1.3 g, 9.72 mmol) and the resulting mixture was stirred at reflux for 60 hours. After cooling to room temperature, the solution was poured into ethyl acetate (40 mL), washed with water (40 mL), dried over sodium sulfate and evaporated to dryness. Column chromatography on silica gel using hexane/ethyl acetate (4:1, 2:1 and 1:1) provided the title compound as a syrup (0.65 g, 30%).

후처리

  1. temperatureat reflux for 60 hours
  2. washwashed with water (40 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated to dryness

출처 및 근거

ORD 기록
ord-221c90edee9d436da453310cff08c10e
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05654431

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