Imidazole → 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester

HRID 2105328노트

반응식

HRID 2105328 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1[CH:26]=[CH:25]N=C1.[Cl-].[NH4+]>CN(C)C=O>[CH2:25]([O:12][C:11]([C:6]1[NH:7][C:8]2[C:4]([CH:5]=1)=[CH:3][C:2]([O:1][Si:18]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20])=[CH:10][CH:9]=2)=[O:13])[CH3:26]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 889585-Hydroxyindole-2-carboxylic acid

생성물 1

HCID 226767305-(tert-butyl-dimethyl-silanyloxy)-1H-indole-2-carboxylic acid ethyl ester수율 98.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To the solution of 10.0 g (49.0 mmol) 5-hydroxyindole-2-carboxylic acid (commercially available) in 30 ml N,N-dimethylformamide, 7.7 g (51.1 mmol) tert-butyldimethylchlorosilane and 3.5 g (51.4 mmoL) imidazole was added. After 1 hour, the solution was poured on 10% aqueous ammonium chloride solution and was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2 v/v) as eluant to give 15.3 g (98.5%) of the compound as a white solid.

후처리

  1. extractionwas extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography over silica gel with ethyl acetate:n-hexane (1:2 v/v) as eluant

출처 및 근거

ORD 기록
ord-f873a1f4b3a745e4a728a1816f38f6ec
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579351B2

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