Benzene, 1-bromo-3-(trifluoromethyl)- → 1-(4-Cyclopropylpyridin-3-yl)-3-(3-(trifluoromethyl) phenyl)imidazolidin-2-one

HRID 523532

Reaktionsgleichung

Reaktionsgleichung von HRID 523532
[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][NH:12][C:11]2=[O:15])[CH2:3][CH2:2]1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH:1]1([C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]2[CH2:14][CH2:13][N:12]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[CH:18]=3)[C:11]2=[O:15])[CH2:3][CH2:2]1

Komponenten

7

Edukt 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 709820071-(4-Cyclopropylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 665764851-(4-Cyclopropylpyridin-3-yl)-3-(3-(trifluoromethyl) phenyl)imidazolidin-2-oneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using analogous reagents and reaction conditions as described in Example 1 above, 1-(4-cyclopropylpyridin-3-yl)imidazolidin-2-one (I-1d: 150 mg, 0.738 mmol) was reacted with 1-bromo-3-(trifluoromethyl)benzene (831 mg, 3.69 mmol), 1,4-dioxane (10 mL), copper iodide (14.0 mg, 0.073 mmol), trans-N,N′-dimethylcyclohexane-1,2-diamine (8.4 mg, 0.073 mmol) and potassium phosphate (469.9 mg, 2.21 mmol) to afford the crude product. Purification by column chromatography on silica gel (1.5% methanol in CHCl3) afforded 205 mg of the product (80% yield).

Aufarbeitung

  1. customreagents and reaction conditions
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (1.5% methanol in CHCl3)

Quellen und Nachweise

ORD-Eintrag
ord-f5167e4067e04c5c90cbeb8a8019c711
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339501B2

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