Nitromalonaldehyde → 5-Nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine

HRID 1521734

Reaktionsgleichung

Reaktionsgleichung von HRID 1521734
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:11]([NH2:12])=[CH:10][CH:9]=[N:8]2)[CH2:3][CH2:2]1.[N+:13]([CH:16]([CH:19]=O)[CH:17]=O)([O-:15])=[O:14]>C(O)(=O)C>[N+:13]([C:16]1[CH:17]=[C:10]2[CH:9]=[N:8][N:7]([CH:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:11]2=[N:12][CH:19]=1)([O-:15])=[O:14]

Komponenten

4

Edukt 2

HCID 313475NitromalonaldehydeHCID 436086621-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine

Produkt 1

HCID 672364995-Nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridineAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
108 °C

Versuchsvorschrift

To a solution of 1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-5-amine (1.6 g, 9.6 mmol) in 70% acetic acid (15 mL) is added nitromalonaldehyde (1.3 g, 9.6 mmol) and the reaction mixture is heated to 108° C. for 3 h. The solvent is evaporated under reduced pressure and the residue is purified by flash column chromatography using a gradient of 20% ethyl acetate/petroleum ether to afford the title compound as a pale yellow solid (1.6 g, 70%).

Aufarbeitung

  1. customThe solvent is evaporated under reduced pressure
  2. customthe residue is purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d3926915f8d44ca7b63da0edc03c4479
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073926B2

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