Dimethylformamide → 2-Ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-2H-pyrazolo[4,3-b]pyridine

HRID 572161Notes

Reaction equation

HRID 572161 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:18]([CH2:26][CH3:27])[N:19]=[C:20]3[CH:25]=[CH:24][CH:23]=[N:22][C:21]=23)=[CH:13][CH:12]=1.IC.[C:30](=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>O>[CH2:26]([N:18]1[C:17]([C:14]2[CH:15]=[CH:16][C:11]([O:10][C:2]3[N:1]([CH3:30])[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=3)=[CH:12][CH:13]=2)=[C:21]2[N:22]=[CH:23][CH:24]=[CH:25][C:20]2=[N:19]1)[CH3:27]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 86704970HCID 86704970, compound

Product 1

HCID 867049712-Ethyl-3-{4-[(1-methyl-1H-benzimidazol-2-yl)oxy]phenyl}-2H-pyrazolo[4,3-b]pyridineYield 92.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-[4-(1H-benzimidazol-2-yloxy)phenyl]-2-ethyl-2H-pyrazolo[4,3-b]pyridine (25 mg) obtained in Example 3, iodomethane (5.72 μl), cesium carbonate (34.4 mg) and DMF (1 ml) was stirred at room temperature for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) and recrystallized from ethyl acetate/hexane to give the title compound (24.0 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  6. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-2d4c50df78a84e8199ac31a04b26ac46
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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