4-Iodo-1-tritylimidazole → HCID 178423886, compound

HRID 2055122Notes

Reaction equation

HRID 2055122 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]([CH3:37])=[N:35][CH:36]=1>C1COCC1.ClCCl.[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>[NH:5]1[CH:6]=[C:2]([C:31]2[CH:32]=[CH:33][C:34]([CH3:37])=[N:35][CH:36]=2)[N:3]=[CH:4]1

Participants

8

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 12010205-Bromo-2-methylpyridineHCID 178418443HCID 178418443, compound

Product 1

HCID 178423886HCID 178423886, compoundYield 63%

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

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-methylpyridine (1.2 eq) were added to the reaction mixture. Following that, the reaction mixture was heated in a 70° C. oil bath overnight. Upon cooling, the reaction was diluted with dichloromethane and washed with a EDTA buffer (at approximately pH 9), NaCl, dried over sodium sulfate, filtered and concentrated. The crude product was disolved in ethanol and concentrated HCl was added to the solution at room temperature. The reaction mixture was heated in a 50° C. oil bath for 2 hours. Upon cooling, the reaction was filtered and washed with ethyl ether to yield 5-(1H-imidazol-4-yl)-2-methyl-pyridine (63%). MH+(160)

Workup

  1. stirringAfter stirring for another 90 minutes
  2. temperatureUpon cooling
  3. washwashed with a EDTA buffer (at approximately pH 9), NaCl
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionconcentrated HCl was added to the solution at room temperature
  8. temperatureThe reaction mixture was heated in a 50° C. oil bath for 2 hours
  9. temperatureUpon cooling
  10. filtrationthe reaction was filtered
  11. washwashed with ethyl ether

Sources & evidence

ORD record
ord-82ad386a6f0943d0973879553f08fe19
Source dataset
uspto-grants-2008_02
Patent number
US07332476B2

Reaction notes

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