3-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazole → 1-((6-isopropylpyridin-2-yl)methyl)-1H-indazol-4-amine

HRID 706727Notes

Reaction equation

HRID 706727 reaction equation
Br[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[N:16]=2)[N:3]=1>CCO.[OH-].[OH-].[Pd+2]>[CH:21]([C:17]1[N:16]=[C:15]([CH2:14][N:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[C:9]([NH2:11])[C:10]=3[CH:2]=[N:3]2)[CH:20]=[CH:19][CH:18]=1)([CH3:23])[CH3:22]

Participants

4

Reactant 1

HCID 679758823-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazole

Product 1

HCID 679763201-((6-isopropylpyridin-2-yl)methyl)-1H-indazol-4-amineYield 68%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To 3-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazole (2.10 g, 5.60 mmol) in EtOH (30 mL) was added Pd(OH)2/C (1.21 g, 1.72 mmol). The reaction mixture purged with N2 and H2 three times each. The reaction was then charged with H2 to 45 psi. The reaction mixture was stirred for 4 hours and filtered through Celite®. The Celite® was washed with EtOH (200 mL) and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (EtOAc/hexane, 2:1) to give the desired product (68%).

Workup

  1. customThe reaction mixture purged with N2 and H2 three times each
  2. additionThe reaction was then charged with H2 to 45 psi
  3. filtrationfiltered through Celite®
  4. washThe Celite® was washed with EtOH (200 mL)
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (EtOAc/hexane, 2:1)

Sources & evidence

ORD record
ord-b693734de79e4387a225ee3de344c8c8
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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