Water → 6-Bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine

HRID 1372927

Reaktionsgleichung

Reaktionsgleichung von HRID 1372927
[H-].[Na+].[C:3]1([CH3:14])[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][NH:12][CH:13]=2)=[CH:5][CH:4]=1.[Br:15][C:16]1[N:17]=[C:18](Br)[C:19]2[N:20]([CH:22]=[CH:23][N:24]=2)[CH:21]=1.O>CN(C=O)C.C(OCC)C>[Br:15][C:16]1[N:17]=[C:18]([N:12]2[CH:13]=[C:9]([C:6]3[CH:5]=[CH:4][C:3]([CH3:14])=[CH:8][CH:7]=3)[N:10]=[CH:11]2)[C:19]2[N:20]([CH:22]=[CH:23][N:24]=2)[CH:21]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazineHCID 178423883HCID 178423883, Verbindung

Produkt 1

HCID 210728866-Bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazineAusbeute 84,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (NaH) (144 milligrams (mg) of a 60% dispersion in mineral oil) is added to a solution of 4-p-tolyl-1H-imidazole (571 mg) in N,N,-dimethylformamide (DMF) (10 ml) and the mixture is stirred at room temperature (rt) for 0.5 hr. A solution of 6,8-dibromoimidazo[1,2-a]pyrazine (3) (1.0 g) in DMF (10 ml) is added. The mixture is stirred at room temperature (rt) for 16 hr. Water (50 ml) is added and the mixture is extracted with ethyl acetate (3×70 ml); extracts are washed with water (2×50 ml) and brine (1×50 ml), dried over magnesium sulfate (MgSO4), and evaporated in vacuo to give a waxy solid. The solid is slurried with a little diethyl ether and filtered to give 6-Bromo-8-(4-p-tolyl-imidazol-1-yl)-imidazo[1,2-a]pyrazine (4) (1.08 g) as a light brown solid.

Aufarbeitung

  1. stirringThe mixture is stirred at room temperature (rt) for 16 hr
  2. extractionthe mixture is extracted with ethyl acetate (3×70 ml)
  3. washextracts are washed with water (2×50 ml) and brine (1×50 ml)
  4. dry with materialdried over magnesium sulfate (MgSO4)
  5. customevaporated in vacuo
  6. customto give a waxy solid
  7. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-dfd4e2d547584077899f362d469a5d8e
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160885B2

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