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

HRID 2361334ノート

反応式

HRID 2361334 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
125 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b580450737e049d7af7f8a2f2b56d257
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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