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

HRID 2055126Notes

Reaction equation

HRID 2055126 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-29fcd29720de4039a6dc8a5868f39ba8
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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