Potassium Carbonate → 1-(3-fluorobenzyl)-5-nitro-1H-indazole

HRID 38510

Reaktionsgleichung

Reaktionsgleichung von HRID 38510
[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].C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23]Br>C1COCC1>[F:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][CH:27]=1)[CH2:23][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 680073-Fluorobenzyl bromide

Produkt 1

HCID 219664901-(3-fluorobenzyl)-5-nitro-1H-indazoleAusbeute 35,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

5-Nitroindazol (10.0 g, 61.3 mmol) was dissolved in THF (100 mL). Potassium carbonate (25.4 g, 184 mmol) and 3-fluorobenzylbromide (12.7 g, 67.4 mmol) were added, and the mixture was heated to reflux for 3 h. The solvent was removed in vacuo, and the residue was dissolved in ethyl acetate (150 mL) and extracted with water (200 mL). The aqueous layer was extracted twice with ethyl acetate (100 mL each). The combined organic layers were dried over sodium sulfate, and the solvent was removed in vacuo. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1) to yield 6.55 g (39%) of the title compound (less polar component) and 5.84 g (35%) of the regioisomeric 2H-indazole derivative (more polar component).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (150 mL)
  5. extractionextracted with water (200 mL)
  6. extractionThe aqueous layer was extracted twice with ethyl acetate (100 mL each)
  7. dry with materialThe combined organic layers were dried over sodium sulfate
  8. customthe solvent was removed in vacuo
  9. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-eced96baf29e45a89f35dbfc2d2f9206
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524722B2

Verknüpfte Notizen

Wird geladen…