4-Toluenesulfonyl chloride → 5-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indole

HRID 1954234노트

반응식

HRID 1954234 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][OH:14].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13][O:14][S:21]([C:18]1[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=1)(=[O:23])=[O:22]

참가 물질

4

반응물 2

HCID 73974-Toluenesulfonyl chlorideHCID 150205413-(5-fluoro-1H-indol-3-yl)propan-1-ol

생성물 1

HCID 150205425-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indole수율 79%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

To a stirred solution of 3-(5-fluoro-1H-indol-3-yl)-propan-1-ol (2.90 g, 15.0 mmol) in pyridine (15.0 mL) was added p-toluenesulfonyl chloride (7.1 g, 37.5 mmol) at room temperature. After stirring for 30 minutes at room temperature, the reaction mixture was poured to 200 mL of ice water. The aqueous was extracted with ethyl acetate and the combined organic extracts were washed with 1N HCl and brine. The resulting material was dried over anhydrous sodium sulfate, filtered, and the solvent was concentrated under vacuum. The crude product was purified by silica gel column chromatography (ethyl acetate/hexane, 3/7) to give 4.1 g (79%) of the title compound as a solid: mp 74° C. (Lit. mp 99° C.; EP 464604 A2).

후처리

  1. extractionThe aqueous was extracted with ethyl acetate
  2. washthe combined organic extracts were washed with 1N HCl and brine
  3. dry with materialThe resulting material was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe solvent was concentrated under vacuum
  6. customThe crude product was purified by silica gel column chromatography (ethyl acetate/hexane, 3/7)

출처 및 근거

ORD 기록
ord-ecb3832e6f79475ab593d26880ab7ce8
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06121307

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