Water → HCID 178428762, Verbindung

HRID 396133

Reaktionsgleichung

Reaktionsgleichung von HRID 396133
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[C:11]2[CH:17]([CH3:19])[CH3:18].F[C:21]1[C:26]([CH3:27])=[CH:25][C:24]([N+:28]([O-:30])=[O:29])=[CH:23][C:22]=1[CH3:31].O>CS(C)=O>[CH3:27][C:26]1[CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=[C:22]([CH3:31])[C:21]=1[O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[C:11]2[CH:17]([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 113672322-Fluoro-1,3-dimethyl-5-nitrobenzeneHCID 178440410HCID 178440410, Verbindung

Produkt 1

HCID 178428762HCID 178428762, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

86 mg (0.624 mmol) of potassium carbonate are added to a solution of 110 mg (0.624 mmol) of 5-hydroxy-3-isopropyl-1H-indazole in 5 ml of DMSO and the mixture is stirred for 1 h. After addition of 106 mg (0.624 mmol) of 4-fluoro-3,5-dimethylnitrobenzene in portions, the mixture is then firstly stirred at room temperature for 2 h, then at 100° C. for 3 h. After cooling to room temperature, the mixture is added to 10 ml of water and the aqueous phase is extracted 3× with ethyl acetate. The combined organic extracts are washed with water and satd NaCl soln, dried over sodium sulphate and concentrated in vacuo. By purification of the resulting residue on silica gel (cyclohexane/ethyl acetate 3:1), 84 mg (41%) of 5-(2,6-dimethyl-4-nitrophenoxy)-3-isopropyl-1H-indazole are obtained.

Aufarbeitung

  1. stirringthe mixture is then firstly stirred at room temperature for 2 h
  2. waitat 100° C. for 3 h
  3. extractionthe aqueous phase is extracted 3× with ethyl acetate
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customBy purification of the resulting residue on silica gel (cyclohexane/ethyl acetate 3:1), 84 mg (41%) of 5-(2,6-dimethyl-4-nitrophenoxy)-3-isopropyl-1H-indazole
  8. customare obtained

Quellen und Nachweise

ORD-Eintrag
ord-a94299fbacbc437c8157b2f9a66ef923
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06608049B2

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