Sodium Hydroxide → 1H-Pyrazolo[3,4-c]pyridine

HRID 2112574Notes

Reaction equation

HRID 2112574 reaction equation
[N:1]1(C(=O)C)[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1.[OH-].[Na+]>O1CCCC1.CO.O>[NH:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[N:2]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 450862091-Acetylpyrazolo[3,4-c]pyridine

Product 1

HCID 64514411H-Pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-pyrazolo[3,4-c]pyridin-1-yl-ethanone (20.2 mg, 0.17 mmol, 1 equiv) in tetrahydrofuran (2 mL) and methanol (0.5 mL) was added sodium hydroxide aqueous solution (2M, 0.25 mL). The reaction solution was stirred at room temperature for 1 hr and then concentrated in vacuo to provide a crude residue. The crude residue was diluted with water (20 mL) and extracted with dichloromethane (2×100 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 1H-pyrazolo[3,4-c]pyridine as white powder, which used without further purification: LCMS (ES) M+H 120.3, Rf 0.22 min (Agilent Zorbax SB-C18, 2.1×50 mm, 5μ, 35° C., 1 ml/min flow rate, a 2.5 min gradient of 20% to 100% B with a 1.1 min wash at 100% B; A=0.1% formic acid /5% acetonitrile /94.9% water, B=0.1% formic acid /5% water/94.9% acetonitrile).

Workup

  1. concentrationconcentrated in vacuo
  2. customto provide a crude residue
  3. extractionextracted with dichloromethane (2×100 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-924645b2632f44a8b65672377c83f3bc
Source dataset
uspto-grants-2009_04
Patent number
US07524845B2

Reaction notes

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