6-(2-methoxyethoxy)-1H-indole → Benzyl 2-fluoro-3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate

HRID 2361334노트

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HRID 2361334 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[C:13]2[C:9]([CH:10]=[CH:11][NH:12]2)=[CH:8][CH:7]=1.[F:15][C:16]1[C:21](/[CH:22]=[CH:23]/[N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=[CH:18][C:17]=1[NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[F:15][C:16]1[C:21]([CH:22]([C:10]2[C:9]3[C:13](=[CH:14][C:6]([O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=3)[NH:12][CH:11]=2)[CH2:23][N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=[CH:18][C:17]=1[NH:27][C:28](=[O:37])[O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

4

반응물 2

HCID 679948936-(2-methoxyethoxy)-1H-indoleHCID 70651607(E)-Benzyl 2-fluoro-3-(2-nitrovinyl)phenylcarbamate

생성물 1

HCID 67994845Benzyl 2-fluoro-3-(1-(6-(2-methoxyethoxy)-1H-indol-3-yl)-2-nitroethyl)phenylcarbamate수율 69.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
125 °C

실험 절차

6-(2-Methoxyethoxy)-1H-indole (1.198 g, 6.26 mmol) and (E)-benzyl 2-fluoro-3-(2-nitrovinyl)phenylcarbamate (1.651 g, 5.22 mmol) were dissolved in THF (50 mL) and concentrated in vacuo, and the mixture was heated at 125° C. overnight. The reaction was cooled to room temperature, and the crude product was purified by flash chromatography (solid loading) using an ISCO 220 g column eluting with 15-75% EtOAc/hexanes to give the desired product (1.888 g, 3.61 mmol, 69.2% yield) as a light orange foam.

후처리

  1. concentrationconcentrated in vacuo
  2. temperatureThe reaction was cooled to room temperature
  3. customthe crude product was purified by flash chromatography (solid loading)
  4. washeluting with 15-75% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-b580450737e049d7af7f8a2f2b56d257
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08685969B2

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