Methanol → HCID 178499174, compound

HRID 2409345Notes

Reaction equation

HRID 2409345 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[CH3:13]O>OS(O)(=O)=O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2]1

Participants

4

Reactant 2

HCID 887MethanolHCID 1785249431H-pyrazolo[3,4-b]pyridine-3-carboxylic acid

Product 1

HCID 178499174HCID 178499174, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Procedure

To a solution of 1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (V) (0.39 g, 2.4 mmol) in dry MeOH (10 mL) was added concentrated H2SO4 (4 drops) and refluxed for 6 h under nitrogen. The solution was cooled and the solvent was evaporated under vacuum. The residue was partitioned between DCM and saturated NaHCO3 solution. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified on a flash silica gel column (100% DCM→100:3 DCM:MeOH) to produce methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VI) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDCl3) δ ppm 4.08 (s, 3 H), 7.38 (m, 1 H), 8.63 (dd, J=8.10, 1.51 Hz, 1 H), 8.72 (dd, J=4.62, 1.41 Hz, 1 H); ESIMS found for C8H7N3O2 m/z 178.2 (M+H).

Workup

  1. temperaturerefluxed for 6 h under nitrogen
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. customThe residue was partitioned between DCM and saturated NaHCO3 solution
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified on a flash silica gel column (100% DCM→100:3 DCM:MeOH)

Sources & evidence

ORD record
ord-351915be048a4801a441a73bcc83b923
Source dataset
uspto-grants-2014_08
Patent number
US08815897B2

Reaction notes

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