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3-Bromopyridine → 3-(4-Methyl-1H-imidazol-5-yl)pyridine

HRID 353772
Notes
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Reaction equation

HRID 353772 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)[C:6]=1[CH3:7].C([Mg]Br)C.Br[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1>C1COCC1.[Cl-].[Zn+2].[Cl-].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:7][C:6]1[NH:5][CH:4]=[N:3][C:2]=1[C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 122863-BromopyridineHCID 235114374-Iodo-5-methyl-1-trityl-1H-imidazoleHCID 178418443HCID 178418443, compound

Product 1

HCID 235114243-(4-Methyl-1H-imidazol-5-yl)pyridineYield 92%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalyst
HCID 178418397
HCID 178418397, compound
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Iodo-5-methyl-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 3-bromopyridine (1.2 eq) were added to the reaction mixture. Subsequent reaction conditions were performed as in Example 73 to give 3-(5-methyl-1H-imidazol-4-yl)-pyridine (92%). MH+(160).

Workup

  1. stirringAfter stirring for another 90 minutes
  2. customSubsequent reaction conditions

Sources & evidence

ORD record
ord-42ed36905f264e8881a7a0259c230336
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