Sodium hydride → 2-(2-tetrahydrofuranyl)-5-methanesulfonyl-1-(4-fluorobenzyl)-1H-indole

HRID 1432235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1432235
[O:1]1[CH2:5][CH2:4][CH2:3][CH: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[CH2:5][CH2:4][CH2:3][CH: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 225044162-(2-tetrahydrofuranyl)-5-methanesulfonyl-1H-indole2×

Produkt 1

HCID 98208782-(2-tetrahydrofuranyl)-5-methanesulfonyl-1-(4-fluorobenzyl)-1H-indole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Example 13: (2) (113 mg) in N,N-dimethylformamide (5 ml), 60% sodium hydride (25.6 mg) was added under nitrogen atmosphere at 0° C. and the mixture was stirred for 30 minutes, followed by addition of 4-fluorobenzyl bromide (121 mg), and the mixture was stirred for 1 hour. The reaction solution was then poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel preparative thin-layer chromatography (hexane:ethyl acetate-=1:1) to obtain 139 mg of the desired product as a white powder.

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Quellen und Nachweise

ORD-Eintrag
ord-b205cc151a6e42dbb681ab1e96f144db
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612070B2

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