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

HRID 2256393

反応式

HRID 2256393 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-221c90edee9d436da453310cff08c10e
出典データセット
uspto-grants-1997_08
特許番号
US05654431

関連ノート

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