Water → 1-benzyl-3-iodo-4-methoxy-1H-pyrazolo[4,3-c]pyridine

HRID 2206242Notes

Reaction equation

HRID 2206242 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12](Cl)[C:11]=2[C:10]([I:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][OH:20].C[O-].[Na+].O>CO>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][N:13]=[C:12]([O:20][CH3:19])[C:11]=2[C:10]([I:18])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 23694274Sodium methanolate methanolHCID 1179879911-benzyl-4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 1179878231-benzyl-3-iodo-4-methoxy-1H-pyrazolo[4,3-c]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 1-benzyl-4-chloro-3-iodo-1H-pyrazolo[4,3-c]pyridine (3.7 g) in methanol (40 mL) was added sodium methoxide methanol solution (1.5 M, 27 mL) at room temperature, and the reaction mixture was refluxed overnight. The reaction mixture was added to water at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was washed with petroleum ether to give the title compound (3.6 g).

Workup

  1. temperaturethe reaction mixture was refluxed overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe obtained residue was washed with petroleum ether

Sources & evidence

ORD record
ord-d9f9e5d97f4b489bbe507d58667116ae
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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