Sodium hydride → methyl 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetate

HRID 571192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 571192
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 27775236-(Trifluoromethyl)indole

Produkt 1

HCID 86681612methyl 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetateAusbeute 34,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-(trifluoromethyl)-1H-indole (250 mg, 1.350 mmol) in dry DMF (3 ml), sodium hydride (60% w/w dispersion in mineral oil, 64.8 mg, 1.620 mmol) was added at room temperature. After 10 minutes, methyl 2-bromoacetate (150 μl, 1.620 mmol) was added and the mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the crude was purified by flash chromatography on silica gel column (hexane/ethyl acetate 90/10) to afford methyl 2-(6-(trifluoromethyl)-1H-indol-1-yl)acetate (120 mg, 0.467 mmol, 34.6% yield). MS/ESI+ 258.1 [MH]+.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customthe crude was purified by flash chromatography on silica gel column (hexane/ethyl acetate 90/10)

Quellen und Nachweise

ORD-Eintrag
ord-1705f63dbd164abe8be77e1f578f430d
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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