4-Iodo-1-tritylimidazole → 2-(1H-imidazol-4-yl)pyrazine

HRID 353771

Reaktionsgleichung

Reaktionsgleichung von HRID 353771
I[C:2]1[N:3]=[CH:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1.C([Mg]Br)C.Br[C:31]1[N:32]=[CH:33][CH:34]=[N:35][CH:36]=1>C1COCC1.[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH:5]1[CH:6]=[C:2]([C:31]2[CH:36]=[N:35][CH:34]=[CH:33][N:32]=2)[N:3]=[CH:4]1

Komponenten

7

Edukt 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 6428002-BromopyrazineHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 1784207612-(1H-imidazol-4-yl)pyrazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3007855ZincchlorideKatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-Iodo-1-trityl-1H-imidazole (1 eq) in THF at room temperature was added ethylmagnesium bromide (1.2 eq) under dry conditions. After stirring for 90 minutes, zinc chloride (1.2 eq) was added to the reaction mixture. After stirring for another 90 minutes, tetrakis(triphenylphosphine) palladium (10%) and 5-bromopyrazine (1.3 eq) were added to the reaction mixture. Subsequent reaction conditions and work up are as described previously in Example 73, the resulting solid 2-(1H-Imidazol-4-yl)-pyrazine (37%) was collected by filtration. MH+(147).

Aufarbeitung

  1. stirringAfter stirring for another 90 minutes
  2. customSubsequent reaction conditions and work
  3. filtrationthe resulting solid 2-(1H-Imidazol-4-yl)-pyrazine (37%) was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-2ffb63a6393a408bb6de2ae981e79900
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756359B2

Verknüpfte Notizen

Wird geladen…