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

HRID 1692889노트

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HRID 1692889 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 25517Ammonium Chloride용매

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온도
0 °C

실험 절차

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.).

후처리

  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)

출처 및 근거

ORD 기록
ord-eabc90a1e73344bfbf6242cdad357227
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08158625B2

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