Water → 5-nitro-1-(pyridin-2-ylmethyl)-1H-indazole

HRID 38547

Reaktionsgleichung

Reaktionsgleichung von HRID 38547
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].Cl.Cl[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].O>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[N:8]=[CH:7]2)([O-:3])=[O:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 23392Picolyl chloride hydrochloride

Produkt 1

HCID 224961495-nitro-1-(pyridin-2-ylmethyl)-1H-indazoleAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Nitroindazole (10.0 g, 61.3 mmol) was dissolved in THF (100 mL), and 2-(chloromethyl)pyridine hydrochloride (8.60 g, 52.4 mmol) and potassium carbonate (24.4 g, 184 mmol) were added. The mixture was heated for 4 h to 75° C. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate) to yield 6.73 g (43%) of the title compound.

Aufarbeitung

  1. temperatureThe mixture was heated for 4 h to 75° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography on silica gel (eluent: gradient cyclohexane/ethyl acetate 1:1 to ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-91d9d9e2622743368ade6bd13677bb0a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524722B2

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