Sodium Hydroxide → HCID 86703419, compound

HRID 1854041Notes

Reaction equation

HRID 1854041 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:15]([O:17]CC)=[O:16])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=1.[OH-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[C:4]([C:15]([OH:17])=[O:16])[C:5]2[C:10]([CH3:11])=[N:9][N:8]([CH:12]([CH3:14])[CH3:13])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86703418HCID 86703418, compound

Product 1

HCID 86703419HCID 86703419, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 6-bromo-1-isopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (0.6 g, 1.84 mmol) in EtOH (10 mL), aqueous NaOH (0.11 g, 2.76 mmol, in 5 mL water) was added and reaction mixture stirred at 60° C. for 1 h. After completion of the reaction, ethanol was removed under reduced pressure and it was acidified using 10% citric acid solution. Extraction was carried out using 5% MeOH/DCM. The combined organic layers were washed with water & dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford target compound (0.35 g., 63.8%), which was not purified further.

Workup

  1. customreaction mixture
  2. customwas removed under reduced pressure and it
  3. extractionExtraction
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford target compound (0.35 g., 63.8%), which
  9. customwas not purified further

Sources & evidence

ORD record
ord-7e8cfe795664446bba89b4c69fdbbe75
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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