Cesium carbonate → 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

HRID 80599

Reaktionsgleichung

Reaktionsgleichung von HRID 80599
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[C:14]1[CH:15]=[C:16]([CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=1)[NH2:17].N1C2C(C(=O)C)CCCC=2C=CC=1>[Cu]I.CN(C=O)C>[CH3:1][C:2]1[N:3]=[CH:4][N:5]([C:14]2[CH:20]=[C:19]([C:21]([F:22])([F:24])[F:23])[CH:18]=[C:16]([NH2:17])[CH:15]=2)[CH:6]=1

Komponenten

7

Edukt 4

HCID 10796Cesium carbonateHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 426044521-(5,6,7,8-Tetrahydroquinolin-8-yl)ethan-1-oneHCID 178418800HCID 178418800, Verbindung

Produkt 1

HCID 120028253-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)anilineAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a pressure tube with one end sealed, add 190 mg CuI (1 mmol), 1.64 g 4-methyl-1H-imidazole (20 mmol), 3.25 g Cs2CO3 (10 mmol), and after Nitrogen replacement, add 2.40 g 3-bromo-5-(trifluoromethyl)aniline (10 mmol), 350 mg 1-(5,6,7,8-tetrahydroquinolin-8-yl)ethanone (2 mmol) and 30 mL DMF was added into a flask. The mixture was stirred at 110° C. for 18 h under sealing. After cooling to room temperature, the solvent was removed under vacuum and the residue was purified by column chromatography to afford 2.19 g desired product (91%).

Aufarbeitung

  1. customIn a pressure tube with one end sealed
  2. additionwas added into a flask
  3. temperatureAfter cooling to room temperature
  4. customthe solvent was removed under vacuum
  5. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a685fed84c2c492e928d694112f66e81
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846671B2

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