Cesium carbonate → [6-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester

HRID 915382노트

반응식

HRID 915382 반응식
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:24]([O:28][C:29](=[O:32])[CH2:30]Br)([CH3:27])([CH3:26])[CH3:25]>CN(C=O)C>[C:24]([O:28][C:29](=[O:32])[CH2:30][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])[CH:15]=2)[CH:11]=[CH:12]1)([CH3:27])([CH3:26])[CH3:25]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 222508166-((tert-butyldimethylsilyl)oxy)-1H-indole

생성물 1

HCID 69279688[6-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester수율 75.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To an ice cold solution of 6-(tert-butyl-dimethyl-silanyloxy)-1H-indole (13 g, 52.5 mmol) and cesium carbonate (18.8 g, 57.8 mmol) in DMF (130 ml) under an argon atmosphere was added bromo-acetic acid tert-butyl ester (8.5 ml, 57.8 mmol). The mixture was naturally warmed to room temperature, stirred for 14 h, poured onto 2 N HCl/ice water 1/1 and extracted two times with ethyl acetate. The combined organic layers were washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography (silica gel, heptane/AcOEt) to give 14.3 g (39.6 mmol, 75%) of the title compound as yellow oil.

후처리

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography (silica gel, heptane/AcOEt)

출처 및 근거

ORD 기록
ord-1929db2137ea48d3a1d8d763875bd9c4
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265149B2

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