1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole → 1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amine

HRID 79373Notes

Reaction equation

HRID 79373 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH2:8][N:9]2[C:17]3[C:12](=[C:13]([N+:18]([O-])=O)[CH:14]=[CH:15][CH:16]=3)[C:11]([CH:21]=[CH2:22])=[N:10]2)=[N:3]1>CCO.C(Cl)Cl.[OH-].[OH-].[Pd+2]>[CH3:1][N:2]1[C:6]([CH3:7])=[CH:5][C:4]([CH2:8][N:9]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]([NH2:18])[C:12]=3[C:11]([CH2:21][CH3:22])=[N:10]2)=[N:3]1

Participants

4

Reactant 1

HCID 866722141-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole

Product 1

HCID 672600441-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-3-ethyl-1H-indazol-4-amineYield 93.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21584144Dichloromethane ethanolSolvent

Procedure

To 1-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole (5.15 g, 17.3 mmol) in EtOH/DCM (100 mL/10 mL) was cautiously added palladium hydroxide on carbon (2.2 g, 20% wt). The reaction mixture was purged with nitrogen and hydrogen three times each. The reaction 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 solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography (EtOAc/Hexane 2:1) to provide the product (4.35 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 solution was concentrated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (EtOAc/Hexane 2:1)

Sources & evidence

ORD record
ord-d8fa3f5928fa40bf92fdc126ce8d615a
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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