1-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole → 3-ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amine
Reaktionsgleichung
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]3[C:11](=[C:12]([N+:17]([O-])=O)[CH:13]=[CH:14][CH:15]=3)[C:10]([CH:20]=[CH2:21])=[N:9]2)=[N:3]1>CCO.[OH-].[OH-].[Pd+2]>[CH2:20]([C:10]1[C:11]2[C:12]([NH2:17])=[CH:13][CH:14]=[CH:15][C:16]=2[N:8]([CH2:7][C:4]2[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=2)[N:9]=1)[CH3:21]Komponenten
4
Versuchsvorschrift
To 1-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole (2.36 g, 8.33 mmol) in EtOH (80 mL) was cautiously added palladium hydroxide on carbon (1.5 g, 20% wt). The reaction mixture was purged with nitrogen and hydrogen three times each. The mixture was agitated under H2 (45 psi) for 3 hours. The system was evacuated and purged with nitrogen. The mixture was filtered through Celite® and the filter pad was washed with MeOH/DCM (10:1, 300 mL). The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography (EtOAc/hexanes 2:1) to provide the product (1.52 g).
Aufarbeitung
- customThe reaction mixture was purged with nitrogen and hydrogen three times each
- customThe system was evacuated
- custompurged with nitrogen
- filtrationThe mixture was filtered through Celite®
- washthe filter pad was washed with MeOH/DCM (10:1, 300 mL)
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography (EtOAc/hexanes 2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-6d3fb56cd0fa46b9aec184caa189caf4
- Quelldatensatz
- uspto-grants-2014_09
- Patentnummer
- US08841455B2
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