Sodium Hydroxide → 1H-Pyrazolo[4,3-b]pyridine-5-methanol

HRID 218467Notes

Reaction equation

HRID 218467 reaction equation
[NH:1]1[C:9]2[C:4](=[N:5][C:6]([C:10](OC)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1.CCOCC>[NH:1]1[C:9]2[C:4](=[N:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59763244Methyl 1H-pyrazolo[4,3-b]pyridine-5-carboxylate

Product 1

HCID 597632841H-Pyrazolo[4,3-b]pyridine-5-methanolYield 76.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1H-pyrazolo[4,3-b]pyridine-5-carboxylic acid, methyl ester (420 mg, 2.37 mmol) was dissolved in THF (30 mL) and cooled to 0° C. LiAlH4 (360 mg, 9.48 mmol) was added in one portion. The mixture was stirred at 0° C. for 3 hr, and diluted with ether. 50% NaOH (5 mL) was added to quench the reaction, and the solid was filtered off through Celite. The filtrate was concentrated, and the residue was purified by flash chromatography to afford 1H-pyrazolo[4,3-b]pyridine-5-methanol (270 mg, 76.4%).

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationthe solid was filtered off through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a3d0eb9f03954c208ff630209fd87fa3
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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