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

HRID 1954234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1954234
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-ecb3832e6f79475ab593d26880ab7ce8
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06121307

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