Imidazole → 7-imidazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1098303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1098303
I[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC.[Cl-].[NH4+]>O1CCOCC1.[Cu](I)I>[N:23]1([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[C:7]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[C:19]([F:22])([F:21])[F:20])[NH:8][C:9]3=[O:12])=[CH:4][CH:3]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Komponenten

8

Edukt 5

HCID 795ImidazoleHCID 8070N,N'-DimethylethylenediamineHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 231568037-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Produkt 1

HCID 231567797-imidazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

10.4 mg (0.025 mmol) of the 7-iodo-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Step A, 0.48 mg (0.0025 mmol) of copper iodide (I), 2.0 mg (0.03 mmol) of imidazole, and 11.1 mg (0.0525 mmol) of potassium phosphate were suspended in 0.25 ml of 1,4-dioxane. Then, 2.6 μl of N,N′-dimethylethylenediamine was added to the suspension, and the obtained mixture was then stirred at 110° C. overnight. Thereafter, the reaction solution was cooled to a room temperature, and a saturated ammonium chloride aqueous solution was then added to the reaction solution, followed by extraction with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and was then concentrated. The obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=25:1 to 20:1), so as to obtain 8.3 mg (93%) of 7-imidazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless viscous oily substance.

Aufarbeitung

  1. temperatureThereafter, the reaction solution was cooled to a room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationwas then concentrated
  5. customThe obtained residue was purified by silica gel column chromatography (methylene chloride:methanol=25:1 to 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-67b4d56095544fbb9f9ec40df47c0987
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08143274B2

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