3-Bromopyridine → HCID 178432533, compound

HRID 353773Notes

Reaction equation

HRID 353773 reaction equation
I[C:2]1[N:3](C)[CH2:4][N:5](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:6]=1.[CH2:27]([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>[CH3:27][C:4]1[NH:5][CH:6]=[C:2]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[N:3]=1

Participants

7

Reactant 3

HCID 122863-BromopyridineHCID 23511456HCID 23511456, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 178432533HCID 178432533, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-Iodo-3-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 (1.1 eq) were added to the reaction mixture. Subsequent reaction conditions were performed as in Example 91(b) to provide 3-(2-methyl-1H-imidazol-4-yl)-pyridine (88%) MH+(160).

Workup

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

Sources & evidence

ORD record
ord-e5a14ecb3721444e97d6f9e9b994bb90
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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