4-Iodo-1-tritylimidazole → HCID 178505534, compound

HRID 353769Notes

Reaction equation

HRID 353769 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[CH:32]=[CH:33][C:34]([F:37])=[N:35][CH:36]=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>[F:37][C:34]1[CH:33]=[CH:32][C:31]([C:2]2[N:3]=[CH:4][NH:5][CH:6]=2)=[CH:36][N:35]=1

Participants

7

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 27831685-Bromo-2-fluoropyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 178505534HCID 178505534, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 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-bromo-2-fluoropyridine (1.2 eq) were added to the reaction mixture. Subsequent reaction conditions and work up are as described previously, in Example 73 to afford the solid 2-Fluoro-5-(1H-imidazol-4-yl)-pyridine (46%). MH+(164).

Workup

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

Sources & evidence

ORD record
ord-b50cd01093f94198a5b30cef4e152629
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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