Potassium Carbonate → 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole

HRID 79352

Reaktionsgleichung

Reaktionsgleichung von HRID 79352
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.Br[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[N:3]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 125437332-(Bromomethyl)-6-methylpyridineHCID 178526562HCID 178526562, Verbindung

Produkt 1

HCID 672597623-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazoleAusbeute 90,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-iodo-4-nitro-1H-indazole (172 mg, 0.596 mmol) in dry N,N-dimethylformamide (3 mL) under an atmosphere of dry nitrogen was added 2-(bromomethyl)-6-methylpyridine (122 mg, 0.656 mmol) and potassium carbonate (165 mg, 1.19 mmol) with magnetic stirring. The mixture was stirred at ambient temperature for 3 days. The reaction mixture was diluted with water (20 mL) and extracted into ethyl acetate. The organic phases were combined, washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting material was purified using preparative chromatography on silica, eluting with hexane/ethyl acetate (3:1) to give 3-iodo-1-((6-methylpyridin-2-yl)methyl)-4-nitro-1H-indazole (213 mg).

Aufarbeitung

  1. extractionextracted into ethyl acetate
  2. washwashed with saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting material was purified
  7. washeluting with hexane/ethyl acetate (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-80d33cdb62c84616b0996130b718f4a5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

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