Methyl iodide → HCID 86673613, compound

HRID 1023460Notes

Reaction equation

HRID 1023460 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:9][CH:10]=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:22]I.[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2[N:9]=[CH:10][N:11]([CH3:22])[C:12]=2[C:13]2[CH:14]=[CH:15][C:16]([F:19])=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 178505559HCID 178505559, compound

Product 1

HCID 86673613HCID 86673613, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-4-[5-(4-fluoro-phenyl)-3H-imidazol-4-yl]-pyridine (250 mg, 0.79 mmol) is dissolved in DMF (5.0 mL) and 60% NaH (38 mg, 0.94 mmol) is added. The mixture is stirred for 30 min and methyl iodide (0.098 mL, 1.6 mmol) is added. The reaction is continued for another 1.5 hrs before Saturated NH4Cl aqueous solution (10 mL) is added. The resulting mixture is extracted with EtOAc (3×25 mL). The organic layers are combined and concentrated to give the crude product which is used in the next step without purification.

Workup

  1. additionis added
  2. extractionThe resulting mixture is extracted with EtOAc (3×25 mL)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6d2176149e10408cbd99467fd0e3259c
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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