Water → HCID 178499173, Verbindung

HRID 82063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 82063
[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.C([O-])(=O)C.[Na+].[Br:19]Br.O>C(O)(=O)C>[Br:19][C:8]1[CH:9]=[C:4]2[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:2][NH:1][C:5]2=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24408BromineHCID 517045Sodium AcetateHCID 178499174HCID 178499174, Verbindung

Produkt 1

HCID 178499173HCID 178499173, VerbindungAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of methyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VI) (0.177 g, 1 mmol), sodium acetate (0.492 g, 6 mmol) and bromine (0.308 mL, 6 mmol) in glacial acetic acid (5 mL) was heated overnight at 120° C. in a sealed tube. The solution was cooled and poured into water. The solids formed were filtered, washed with water and dried at room temperature under vacuum. The crude product was purified on a flash silica gel column (100% DCM→100:2 DCM:MeOH) to produce methyl 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylate (VII) as a white solid (78 mg, 0.31 mmol, 30% yield). 1H NMR (CDCl3) δ ppm 3.95 (s, 3 H), 8.62 (d, J=3.01 Hz, 1 H), 8.73 (d, J=3.01 Hz, 1 H); ESIMS Found for C8H6BrN3O2 m/z 256.3 (M+H).

Aufarbeitung

  1. temperatureThe solution was cooled
  2. customThe solids formed
  3. filtrationwere filtered
  4. washwashed with water
  5. customdried at room temperature under vacuum
  6. customThe crude product was purified on a flash silica gel column (100% DCM→100:2 DCM:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-003a1217fafc40f198bed5b0af3cfd44
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846714B2

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