1-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole → 3-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-amine

HRID 79297

Reaction equation

HRID 79297 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([CH2:9][N:10]2[C:18]3[C:13](=[C:14]([N+:19]([O-])=O)[CH:15]=[CH:16][CH:17]=3)[C:12]([CH:22]=[CH2:23])=[N:11]2)[CH:6]=[CH:5][CH:4]=1>CO.[OH-].[OH-].[Pd+2]>[CH2:22]([C:12]1[C:13]2[C:14]([NH2:19])=[CH:15][CH:16]=[CH:17][C:18]=2[N:10]([CH2:9][C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=2)[N:11]=1)[CH3:23]

Participants

4

Reactant 1

HCID 672600471-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole

Product 1

HCID 672592283-ethyl-1-((6-methoxypyridin-2-yl)methyl)-1H-indazol-4-amineYield 79.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 1-((6-methoxypyridin-2-yl)methyl)-4-nitro-3-vinyl-1H-indazole (1.89 g, 6.09 mmol) in MeOH (60 mL) was added Pd(OH)2/C (20 wt %, 400 mg). The reaction mixture was purged with N2 and charge with H2 (45 psi). The reaction mixture was recharged H2 to 45 psi after 45 minute. The reaction was stopped after 5 hours. The reaction mixture was filtered through Celite®, washed with MeOH (200 mL) and concentrated to provide the desired product (1.36 g).

Workup

  1. customThe reaction mixture was purged with N2
  2. additioncharge with H2 (45 psi)
  3. customafter 45 minute
  4. filtrationThe reaction mixture was filtered through Celite®
  5. washwashed with MeOH (200 mL)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a228aba76530405ab6f4c68bf6c1a722
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Linked notes

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