Water → Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylate

HRID 416208노트

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HRID 416208 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:16][CH:15]=2)=[CH:2]1.C(N(C(C)C)CC)(C)C.Br[CH2:36][CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40].O>CS(C)=O>[C:42]([Si:39]([CH3:41])([CH3:40])[O:38][CH2:37][CH2:36][N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]=[CH:21][C:22]([O:24][CH3:25])=[O:23])=[CH:18][CH:19]=1)[CH2:11][CH2:10][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)([CH3:45])([CH3:44])[CH3:43]

참가 물질

6

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 59036879Methyl 3-(4-{[2-(1H-indol-3-yl)-ethylamino]-methyl}-phenyl)-acrylate

생성물 1

HCID 59036876Methyl 3-[4-({[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-[2-(1H-indol-3-yl)-ethyl]-amino}-methyl)-phenyl]-acrylate수율 97.6%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

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온도
52.5 °C

실험 절차

To a stirred solution of 2 (2.82 g, 8.44 mmol) and diisopropylethylamine (2.21 mL, 12.66 mmol) in anhydrous DMSO (22 mL) at room temperature under nitrogen was added (2-bromo-ethoxy)-tert-butyl-dimethylsilane (2.17 mL, 10.12 mmol). The reaction mixture was heated at 50-55° C. for 24 h, poured into water and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2, 15/85, plus a few drops of NH4OH) to afford the title compound 3 (4.06 g, 8.24 mmol, 97% yield) as a dark orange oil.

후처리

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel (AcOEt/CH2Cl2, 15/85, plus a few drops of NH4OH)

출처 및 근거

ORD 기록
ord-1890850da9a748f18d63f8d7eb234db6
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088805B2

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