Dimethylformamide → 4-(4-fluoro-phenoxy)-2-methylsulfanyl-6-(pyridin-3-yloxy)-1H-benzimidazole

HRID 13253Notes

Reaction equation

HRID 13253 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].CI.CN(C)C=O.[F:14][C:15]1[CH:38]=[CH:37][C:18]([O:19][C:20]2[C:28]3[N:27]=[C:26]([SH:29])[NH:25][C:24]=3[CH:23]=[C:22]([O:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:21]=2)=[CH:17][CH:16]=1>C(OCC)(=O)C>[F:14][C:15]1[CH:38]=[CH:37][C:18]([O:19][C:20]2[C:28]3[N:27]=[C:26]([S:29][CH3:1])[NH:25][C:24]=3[CH:23]=[C:22]([O:30][C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:21]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178505885HCID 178505885, compound

Product 1

HCID 231455514-(4-fluoro-phenoxy)-2-methylsulfanyl-6-(pyridin-3-yloxy)-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

30 mg of potassium carbonate and 0.014 ml of methyl iodide were added to a dimethylformamide (1.0 ml) solution of 78 mg of 4-(4-fluoro-phenoxy)-6-(pyridin-3-yloxy)-1H-benzimidazole-2-thiol produced in Example 115, and the reaction liquid was stirred at 0° C. for 30 minutes. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure to obtain the entitled compound.

Workup

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline in order
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure
  6. customto obtain the entitled compound

Sources & evidence

ORD record
ord-f463d4d7b402488a8b1556f973370678
Source dataset
uspto-grants-2010_06
Patent number
US07728025B2

Reaction notes

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