Sodium hydride → 2-(2-Furanyl)-1-(4-fluorobenzyl)-5-methanesulfonylindole

HRID 1814071Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1814071
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2.[H-].[Na+].[F:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1.[Cl-].[NH4+]>CN(C)C=O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:7]([CH2:26][C:25]2[CH:28]=[CH:29][C:22]([F:21])=[CH:23][CH:24]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:10][CH:9]=2

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 680214-Fluorobenzyl bromideHCID 225044472-(2-Furanyl)-5-methanesulfonylindole

Produkt 1

HCID 98206562-(2-Furanyl)-1-(4-fluorobenzyl)-5-methanesulfonylindoleAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Example 8 (6) (150 mg) in N,N-dimethylformamide (6 ml), 60% sodium hydride (34.4 mg) was added at 0° C. under nitrogen atmosphere, and the mixture was stirred for 15 minutes. To the mixture was added 4-fluorobenzyl bromide (160 mg), followed by stirring for 2 hours. After completion of the reaction, the reaction solution was poured into a saturated aqueous ammonium chloride solution, extracted with toluene, washed with a saturated aqueous NaCl solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (methanol:chloroform=1:100) and silica gel preparative thin-layer chromatography (methanol:chloroform=1:100) to obtain 130 mg of the desired product as a pale brown oil.

Aufarbeitung

  1. stirringby stirring for 2 hours
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washwashed with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was separated

Quellen und Nachweise

ORD-Eintrag
ord-7374456a834a4428888e6e344b24e019
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875770B2

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