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

HRID 79364Notes

Reaction equation

HRID 79364 reaction equation
[CH3:1][O:2][C:3]1[C:8]([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:7][CH:6]=[C:5]([CH3:24])[N:4]=1>[OH-].[OH-].[Pd+2].CO>[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:8]2[C:3]([O:2][CH3:1])=[N:4][C:5]([CH3:24])=[CH:6][CH:7]=2)[N:11]=1)[CH3:23]

Participants

4

Reactant 1

HCID 672606771-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole

Product 1

HCID 672595973-ethyl-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-1H-indazol-4-amineYield 29.9%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To 1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-3-vinyl-1H-indazole (395 mg, 1.22 mmol) in a Parr flask was added palladium hydroxide on carbon (171 mg, 20% wt) and MeOH (6 mL) for solubility. The Parr flask was attached to the shaker and applied with 40 psi H2 for seven hours. The reaction mixture was evacuated, purged with nitrogen, filtered through Celite, and the filter pad was rinsed with MeOH. The filtrate was concentrated to a yellow oily residue under reduced pressure. Silica gel chromatography eluting with 1% MeOH, 0.5% NH4OH in DCM gave the product (108 mg).

Workup

  1. customThe reaction mixture was evacuated
  2. custompurged with nitrogen
  3. filtrationfiltered through Celite
  4. washthe filter pad was rinsed with MeOH
  5. concentrationThe filtrate was concentrated to a yellow oily residue under reduced pressure
  6. washSilica gel chromatography eluting with 1% MeOH, 0.5% NH4OH in DCM

Sources & evidence

ORD record
ord-6af71843a4a346c4bf454b16b9e6b0e2
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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