Aluminium lithium hydride → (1H-pyrazolo[3,4-c]pyridin-5-yl)methanol

HRID 218472Notes

Reaction equation

HRID 218472 reaction equation
[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([C:10](OC)=[O:11])[CH:9]=[C:4]2[CH:3]=[N:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH:1]1[C:5]2=[CH:6][N:7]=[C:8]([CH2:10][OH:11])[CH:9]=[C:4]2[CH:3]=[N:2]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59855813Methyl 1H-pyrazolo[3,4-C]pyridine-5-carboxylate

Product 1

HCID 59763243(1H-pyrazolo[3,4-c]pyridin-5-yl)methanolYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1H-pyrazolo[3,4-c]pyridine-5-carboxylic acid, methyl ester (1.5 g, 8.5 mmol) in THF (350 mL) at 0° C. was added LAH (958 mg) in two portions. The reaction was stirred at 0° C. for 1.5 hr, and at rt for 1 hr. The reaction was quenched with con. NaOH at 0° C., and the solid was filtered off and washed with MeOH. The filtrate was concentrated. Purification by column afforded 1H-pyrazolo[3,4-c]pyridine-5-methanol (1.23 g, 96%).

Workup

  1. waitat rt for 1 hr
  2. customThe reaction was quenched with con
  3. filtrationNaOH at 0° C., and the solid was filtered off
  4. washwashed with MeOH
  5. concentrationThe filtrate was concentrated
  6. customPurification by column

Sources & evidence

ORD record
ord-3a1839ae7ce1403e89866ca8eeede9dd
Source dataset
uspto-grants-2012_06
Patent number
US08198456B2

Reaction notes

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