Sodium hydride → 2-Phenoxymethyl-1-(4-trifluoromethylsulfanyl-benzyl)-1H-indole-5-carboxylic acid methyl ester

HRID 131248

Reaktionsgleichung

Reaktionsgleichung von HRID 131248
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:8]2)=[O:4].[H-].[Na+].Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=1)[C:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:8]2)=[O:4]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 27778824-(Trifluoromethylthio)benzyl bromideHCID 597322132-Phenoxymethyl-1H-indole-5-carboxylic acid methyl ester

Produkt 1

HCID 684637372-Phenoxymethyl-1-(4-trifluoromethylsulfanyl-benzyl)-1H-indole-5-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

30 mg of 2-phenoxymethyl-1H-indole-5-carboxylic acid methyl ester were dissolved in 1 ml of THF and treated with 5 mg NaH (60%) at 0° C. for 15 min. 1.2 eq. of 1-bromomethyl-4-trifluoromethylsulfanyl-benzene were added and the reaction stirred for 1.5 h. The solvent was evaporated and the product extracted from methylenchloride/water. The product was purified by preparative HPLC. MS(ISP): 472.5 (M+H)+.

Aufarbeitung

  1. customThe solvent was evaporated
  2. extractionthe product extracted from methylenchloride/water
  3. customThe product was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-8ae9c9914e6e45bca1f42e518d6c7da8
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384945B2

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