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

HRID 79379Notes

Reaction equation

HRID 79379 reaction equation
[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]

Participants

4

Reactant 1

HCID 866722161-((1-methyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole

Product 1

HCID 672599453-ethyl-1-((1-methyl-1H-pyrazol-3-yl)methyl)-1H-indazol-4-amineYield 71.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

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).

Workup

  1. customThe reaction mixture was purged with nitrogen and hydrogen three times each
  2. customThe system was evacuated
  3. custompurged with nitrogen
  4. filtrationThe mixture was filtered through Celite®
  5. washthe filter pad was washed with MeOH/DCM (10:1, 300 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (EtOAc/hexanes 2:1)

Sources & evidence

ORD record
ord-6d3fb56cd0fa46b9aec184caa189caf4
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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