Potassium methoxide → 2-(2,6-dichlorophenyl)-7-methoxy-2H-pyrazolo[4,3-c]pyridine 5-oxide

HRID 626738Notes

Reaction equation

HRID 626738 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:19]=[C:12]2[CH:13]=[N+:14]([O-:18])[CH:15]=[C:16](F)[C:11]2=[N:10]1.[CH3:20][O-:21].[K+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:19]=[C:12]2[CH:13]=[N+:14]([O-:18])[CH:15]=[C:16]([O:21][CH3:20])[C:11]2=[N:10]1

Participants

4

Reactant 2

HCID 23664618Potassium methoxideHCID 696712512-(2,6-Dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5-oxide

Product 1

HCID 696715972-(2,6-dichlorophenyl)-7-methoxy-2H-pyrazolo[4,3-c]pyridine 5-oxideYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 2-(2,6-dichlorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine-5-oxide (1.5 g, 5 mmol) and potassium methoxide (525 mg, 7.5 mmol) in methanol (10 mL) was sealed in a microwave vial, purged with nitrogen and irradiated at 150° C. for 30 minutes in the microwave. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was triturated with ether to afford the title compound as a beige solid (1.32 g, 85% yield). LCMS (Method D): RT=2.31 min, m/z: 310 [M+H+].

Workup

  1. customwas sealed in a microwave vial
  2. custompurged with nitrogen
  3. customirradiated at 150° C. for 30 minutes in the microwave
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-6fbc31e483264916aed9173096fd1abf
Source dataset
uspto-grants-2016_04
Patent number
US09309240B2

Reaction notes

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