Methanol → HCID 178499174, Verbindung

HRID 334456Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 334456
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 178499174HCID 178499174, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidKatalysator

Versuchsvorschrift

To a solution of 1H-pyrazole[3,4-b]pyridine-3-carboxylic acid (XV) (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 aqueous 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→3:97 MeOH:DCM) to produce methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (XVI) as a white solid (382 mg, 2.16 mmol, 90% yield). 1H NMR (CDCl3) δ ppm 4.08 (s, 3H), 7.38 (m, 1H), 8.63 (dd, J=8.10 Hz, J=1.51 Hz, 1H), 8.72 (dd, J=4.62 Hz, J=1.41 Hz, 1H); ESIMS found for C8H7N3O2 m/z 178.2 (M+H).

Aufarbeitung

  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 aqueous 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→3:97 MeOH:DCM)

Quellen und Nachweise

ORD-Eintrag
ord-7b5a921a08c047abb27ade5f96756c47
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883822B2

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