ethyl 2-[3-(4-nitrobenzyl)-1H-indazol-1-yl]acetate → ethyl 2-[3-(4-aminobenzyl)-1H-indazol-1-yl]acetate

HRID 589348Notes

Reaction equation

HRID 589348 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:10]=2)=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:10]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 89590255ethyl 2-[3-(4-nitrobenzyl)-1H-indazol-1-yl]acetate

Product 1

HCID 89590284ethyl 2-[3-(4-aminobenzyl)-1H-indazol-1-yl]acetateYield 53.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.3 g (3.83 mmol) ethyl 2-[3-(4-nitrobenzyl)-1H-indazol-1-yl]acetate was dissolved in 40 mL methanol. 200 mg palladium on carbon was added, and reacted under an atmosphere of H2 at room temperature overnight. It was filtered to remove solid, rotate evaporated to dryness to remove the solvent, and separated by a preparative chromatography to obtain a white solid 630 mg, at a yield of 53.3%.

Workup

  1. customreacted under an atmosphere of H2 at room temperature overnight
  2. filtrationIt was filtered
  3. customto remove solid
  4. customrotate evaporated to dryness
  5. customto remove the solvent
  6. customseparated by a preparative chromatography

Sources & evidence

ORD record
ord-3980d90367aa4ddeb7b4f496eaec4e9a
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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