Potassium Carbonate → 1-(6-Methoxy-naphthalen-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80048

Reaktionsgleichung

Reaktionsgleichung von HRID 80048
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]1[CH2:12][CH2:11][NH:10][C:9]1=[O:13].Br[C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:25][CH3:26])[CH:21]=2)[CH:16]=1.N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+]>[Cu](I)I.O1CCOCC1>[CH3:26][O:25][C:20]1[CH:21]=[C:22]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([N:10]1[CH2:11][CH2:12][N:8]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][C:2]=3[CH3:1])[C:9]1=[O:13])[CH:24]=[CH:23]2

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 787862-Bromo-6-methoxynaphthaleneHCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Produkt 1

HCID 596362541-(6-Methoxy-naphthalen-2-yl)-3-(4-methyl-pyridin-3-yl)-imidazolidin-2-oneAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Using the same reaction conditions as in Example 14, 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 150 mg, 0.847 mmol) was reacted with 2-bromo-6-methoxy-naphthalene (200.74 mg, 0.847 mmol), 1,4-dioxane (15 mL), copper iodide (16.13 mg, 0.0847 mmol), trans-1,2-diamino cyclohexane (0.03 mL, 0.254 mmol) and potassium carbonate (233.97 mg, 1.694 mmol) to afford the crude product. Purification by column chromatography on silica gel (1% MeOH in chloroform) afforded 85 mg of the product (30.08% yield).

Aufarbeitung

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (1% MeOH in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-73a0ba568735417b927110278c60c56f
Quelldatensatz
uspto-grants-2014_09
Patentnummer
USRE045173E1

Verknüpfte Notizen

Wird geladen…