Sodium hydride → 2-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-yl]-1-(2,4-dimethoxy-phenyl)-ethanone

HRID 1394474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394474
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][C:5]2[NH:6][C:7]([CH2:9][C:10]([F:13])([F:12])[F:11])=[N:8][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=1[O:31][CH3:32])=[O:22]>CN(C=O)C>[Cl:16][C:15]1[C:2]([Cl:1])=[CH:3][C:4]2[N:8]([CH2:20][C:21]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=3[O:31][CH3:32])=[O:22])[C:7]([CH2:9][C:10]([F:12])([F:13])[F:11])=[N:6][C:5]=2[CH:14]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 986832-Bromo-1-(2,4-dimethoxyphenyl)ethanoneHCID 116519105,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole

Produkt 1

HCID 444302422-[5,6-Dichloro-2-(2,2,2-trifluoro-ethyl)-benzoimidazol-1-yl]-1-(2,4-dimethoxy-phenyl)-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 5,6-dichloro-2-(2,2,2-trifluoro-ethyl)-1H-benzimidazole (317 mg) in DMF (5 mL) was added sodium hydride (71 mg of 60% in oil dispersion). The resulting mixture was stirred at room temperature for 5 min. To the dark green solution was added 2-bromo-2′,4′-dimethoxyacetophenone (382 mg) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with water, extracted with EtOAc, and dried over Na2SO4. The crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes) to yield the title compound as a white solid.

Aufarbeitung

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customThe crude product was purified by silica gel chromatography (10%-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a1540bbdc98848edb7b9fd3ee290bbe1
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348438B2

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