Sodium Hydroxide → 1-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

HRID 1522526Notes

Reaction equation

HRID 1522526 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([O:20]CC)=[O:19])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:8]=3[N:9]=2)[CH2:3][CH2:2]1.[OH-].[Na+]>C(O)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:18]([OH:20])=[O:19])[C:7]3[C:12]([CH3:13])=[N:11][N:10]([C:14]([CH3:17])([CH3:15])[CH3:16])[C:8]=3[N:9]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68078897ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Product 1

HCID 398706041-tert-butyl-6-cyclopropyl-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-cyclopropyl-1-(1,1-dimethylethyl)-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (278 mg, 0.922 mmol) in ethanol (30 mL) was added sodium hydroxide (3.69 mL, 3.69 mmol) and the contents heated at reflux for 2 hours. The solvent was removed in vacuo, the residue dissolved in 20 mL of water, and acidifed by addition of acetic acid. The contents were extracted with EtOAc (4×30 ml). The combined organic extracts were washed with water, brine, dried over MgSO4, filtered, and concentrated in vacuo. The product was collected as 233 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97-1.12 (m, 4 H), 1.69 (s, 9 H), 2.22-2.41 (m, 3 H), 2.52 (s, 3 H), 7.45 (s, 3 H). LCMS(ES) [M+H]+ 274.2

Workup

  1. temperaturethe contents heated
  2. temperatureat reflux for 2 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue dissolved in 20 mL of water
  5. additionacidifed by addition of acetic acid
  6. extractionThe contents were extracted with EtOAc (4×30 ml)
  7. washThe combined organic extracts were washed with water, brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe product was collected as 233 mg

Sources & evidence

ORD record
ord-9eddfd52459f40cdbca808f60e26895c
Source dataset
uspto-grants-2015_07
Patent number
US09073924B2

Reaction notes

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