Hydrochloric Acid → 1H-Pyrazolo(4,3-b)pyridine

HRID 246052Notes

Reaction equation

HRID 246052 reaction equation
[N:1]1(C(=O)C)[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[OH-].[Na+].Cl>C1COCC1.CO.O>[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 450862101-(1H-pyrazolo[4,3-b]pyridin-1-yl)ethanone

Product 1

HCID 216436531H-Pyrazolo(4,3-b)pyridineYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Pyrazolo[4,3-b]pyridin-1-yl-ethanone (973 mg, 6.04 mmol) was dissolved in THF/MeOH (1:1, 16 mL) and 10% NaOH (1.8 mL) was added. The reaction mixture was stirred at room temperature for 30 min then neutralized with 1.0 M HCl, diluted with water and extracted with EtOAc (2×). The combined organics were washed with brine then dried over MgSO4 and concentrated to afford 687 mg (96%) of 1H-pyrazolo[4,3-b]pyridine as a light yellow solid. 1H NMR (DMSO-d6, 300 MHz): δ (ppm) 13.29 (br. s., 1H), 8.50 (d, J=4.5 Hz, 1H), 8.27 (s, 1H), 8.00 (d, J=8.7 Hz, 1H), 7.34 (dd, J=8.7, 4.5 Hz, 1H).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organics were washed with brine
  3. dry with materialthen dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e6908089cf7542258e5bc0f7ecfd8a89
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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