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

HRID 589365Notes

Reaction equation

HRID 589365 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:10]2)=[CH:6][CH:5]=1)([O-])=O.C(OCC)(=O)C>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:10]2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 89590252ethyl 2-[1-(4-nitrobenzyl)-1H-indazol-3-yl]acetate

Product 1

HCID 89590263ethyl 2-[1-(4-aminobenzyl)-1H-indazol-3-yl]acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Ethyl 2-[1-(4-nitrobenzyl)-1H-indazol-3-yl]acetate (340 mg, 1.04 mmol) was dissolved in methanol (20 mL). 10% Pd/C(20 mg) was added, and reacted under hydrogen atmosphere for half an hour. TLC (petroleum ether:ethyl acetate=2:1) indicated that starting material disappeared. It was filtered to remove solid, rotate evaporated to dryness to remove the solvent. The resulting solid was used for the next step directly.

Workup

  1. customreacted under hydrogen atmosphere for half an hour
  2. filtrationIt was filtered
  3. customto remove solid
  4. customrotate evaporated to dryness
  5. customto remove the solvent

Sources & evidence

ORD record
ord-6332bf328f3942c9b7e436a69537d3ca
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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