Sodium Iodide → 1-Propyl-2-{[2-(2-fluoropyrid-6-yl)-1H-imidazol-1-yl]methyl}-5-cyano-1H-benzimidazole

HRID 895514Notes

Reaction equation

HRID 895514 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[NH:11][CH:12]=[CH:13][N:14]=2)[N:5]=1.[CH2:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:21]=2[N:20]=[C:19]1[CH2:29]Cl)[CH2:16][CH3:17].[I-].[Na+]>CN(C=O)C.O>[CH2:15]([N:18]1[C:22]2[CH:23]=[CH:24][C:25]([C:27]#[N:28])=[CH:26][C:21]=2[N:20]=[C:19]1[CH2:29][N:11]1[CH:12]=[CH:13][N:14]=[C:10]1[C:6]1[N:5]=[C:4]([F:3])[CH:9]=[CH:8][CH:7]=1)[CH2:16][CH3:17]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 223800642-(Chloromethyl)-1-propyl-1H-benzimidazole-5-carbonitrile

Product 1

HCID 98418061-Propyl-2-{[2-(2-fluoropyrid-6-yl)-1H-imidazol-1-yl]methyl}-5-cyano-1H-benzimidazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

To a stirring suspension of sodium hydride (2.25 g of 60% in oil) in DMF (10 mL) at 0° a solution of 2-Fluoro-6-(1H-imidazol-2-yl)-pyridine (7.7 9, 47.2 mmol) in DMF (20 mL) is added. After stirring for 5 minutes, a solution of 1-n-Propyl-2-chloromethyl-5-cyanobenzimidazole (11 g, 47.2 mmol) and sodium iodide (20 mg) in DMF (80 mL) is added. The reaction mixture is stirred for 6 h, gradually warmed to room temperature. The reaction mixture is cooled, water added, the solid collected, rinsed with water and dried to afford the title compound, 1-Propyl-2-{[2-(2-fluoropyrid-6-yl)-1H-imidazol-1-yl]methyl}-5-cyano-1H-benzimidazole.

Workup

  1. additionis added
  2. stirringThe reaction mixture is stirred for 6 h
  3. temperatureThe reaction mixture is cooled
  4. customthe solid collected
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-e6f28846cdac480480f1644bc627e6d3
Source dataset
uspto-grants-2005_07
Patent number
US06916819B2

Reaction notes

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