Benzene, 1-chloro-4-fluoro- → 5-allyloxy-N-(4-chlorophenyl)indole

HRID 342767

Reaktionsgleichung

Reaktionsgleichung von HRID 342767
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)[CH:4]=[CH2:5].F[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1>O1CCCC1>[CH2:3]([O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH:11]=[CH:10]2)[CH:4]=[CH2:5]

Komponenten

5

Edukt 3

HCID 9604Benzene, 1-chloro-4-fluoro-HCID 24758Sodium hydrideHCID 142392305-(prop-2-en-1-yloxy)-1H-indole

Produkt 1

HCID 544104885-allyloxy-N-(4-chlorophenyl)indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of sodium hydride (60%, 254 mg, 6.35 mmol) in 15 mL tetrahydrofuran (THF) was added 5-allyloxyindole (Step A; 1.0 g, 5.77 mmol) in 5 mL THF and the mixture was stirred for 1 hour at ambient temperature. 4-fluorochlorobenzene (0.69 mL, 6.35 mmol) was added and the reaction heated to reflux for 21 hours. After cooling, the reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and the crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane) to provide the title compound.

Aufarbeitung

  1. temperaturethe reaction heated
  2. temperatureto reflux for 21 hours
  3. temperatureAfter cooling
  4. customthe reaction was quenched with saturated aqueous ammonium chloride
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customthe crude residue purified by flash chromatography on silica gel (15% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-795c175dcce247b2aacf26afcf06a6ac
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859051

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