Ethyl Acetate → 1-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine

HRID 1039093Notes

Reaction equation

HRID 1039093 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=3)[C:10]([CH3:20])=[N:9]2)=[CH:5][CH:4]=1.CCOC(C)=O>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][C:13]([NH2:17])=[CH:14][CH:15]=3)[C:10]([CH3:20])=[N:9]2)=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 669271231-(4-methoxybenzyl)-3-methyl-5-nitro-1H-indazole

Product 1

HCID 669270631-(4-methoxybenzyl)-3-methyl-1H-indazol-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-(4-methoxybenzyl)-3-methyl-5-nitro-1H-indazole (275 mg, 0.93 mmol) from Step 1 of this example was dissolved in MeOH (4.6 ml) and EtOAc (10 ml) to give a clear yellow solution. Pd/C (10%, 98 mg) was added, the vessel evacuated and backfilled with hydrogen (3×) and slurry stirred under a hydrogen atmosphere for 30 minutes. The mixture was filtered through CELITE, the filter cake washed with EtOAc (2×40 ml), the filtrates combined and the volatiles removed in vacuum to give the titled compound.

Workup

  1. customthe vessel evacuated
  2. filtrationThe mixture was filtered through CELITE
  3. washthe filter cake washed with EtOAc (2×40 ml)
  4. customthe volatiles removed in vacuum

Sources & evidence

ORD record
ord-c21d29b60fff45bbb0851b95af5c347b
Source dataset
uspto-grants-2013_10
Patent number
US08552022B2

Reaction notes

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