Potassium Carbonate → 3-Bromo-1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-4-nitro-1H-indazole

HRID 79386

Reaktionsgleichung

Reaktionsgleichung von HRID 79386
[Br: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.Cl.Cl[CH2:16][C:17]1[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br: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]([CH2:16][C:17]2[CH:21]=[CH:20][N:19]([CH2:22][CH3:23])[N:18]=2)[N:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67261340HCID 67261340, VerbindungHCID 178526560HCID 178526560, Verbindung

Produkt 1

HCID 672611563-Bromo-1-[(1-ethyl-1H-pyrazol-3-yl)methyl]-4-nitro-1H-indazoleAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a suspension of 3-bromo-4-nitro-1H-indazole (Preparation B; 8.51 g, 35.2 mmol) in DMF (60 mL) was added 3-(chloromethyl)-1-ethyl-1H-pyrazole hydrochloride (6.37 g, 35.2 mmol) and K2CO3 (14.6 g, 106 mmol). The reaction mixture was stirred for 16 hours. Most of DMF was removed under reduced pressure. The remaining residue was diluted with EtOAc (300 mL) and washed with H2O. The organic phase was dried (Na2SO4) and concentrated under reduced pressure. The residue was purified by silica gel chromatography (EtOAc/hexanes 1:5) to provide the product (9.26 g).

Aufarbeitung

  1. customMost of DMF was removed under reduced pressure
  2. additionThe remaining residue was diluted with EtOAc (300 mL)
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (EtOAc/hexanes 1:5)

Quellen und Nachweise

ORD-Eintrag
ord-246425ffe982440fb14903c05f394427
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841455B2

Verknüpfte Notizen

Wird geladen…