Benzenesulfonyl chloride → 6-fluoro-3-iodo-1-(phenylsulfonyl)-1H-indole

HRID 1692889ノート

反応式

HRID 1692889 の反応式
[I:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([F:11])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[Cl-].[NH4+]>[F:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([I:1])=[CH:3][N:4]2[S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])=[CH:9][CH:8]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 177588846-fluoro-3-iodo-1H-indole

生成物 1

HCID 672798376-fluoro-3-iodo-1-(phenylsulfonyl)-1H-indole収率 110.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
0 °C

実験手順

To a cooled (0° C.) solution of 3-iodo-6-fluoroindole (0.50 g, 1.92 mmol) in DMF (10 mL) was added sodium hydride (60% dispersion, 115 mg, 2.87 mmol). The resulting mixture was then stirred at 0° C. for 5 minutes before the addition of benzenesulfonyl chloride (0.37 mL, 2.9 mmol). After stirring at 0° C. for 30 minutes, the reaction was allowed to warm to room temperature and stirred at room temperature for 30 minutes. The reaction mixture was then diluted with saturated ammonium chloride. The aqueous mixture was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (0-50% gradient EtOAc-heptane) to give 6-fluoro-3-iodo-1-(phenylsulfonyl)-1H-indole (0.852 g, quant.).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred at room temperature for 30 minutes
  3. extractionThe aqueous mixture was extracted three times with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (0-50% gradient EtOAc-heptane)

出典と根拠

ORDレコード
ord-eabc90a1e73344bfbf6242cdad357227
出典データセット
uspto-grants-2012_04
特許番号
US08158625B2

反応ノート

読み込み中…