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

HRID 353771
Notes
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Reaction equation

HRID 353771 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3007855ZincchlorideCatalyst
HCID 11979704
Tetrakis(triphenylphosphine)palladium
Catalyst
HCID 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-2ffb63a6393a408bb6de2ae981e79900
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06756359B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes