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

HRID 589368Notes

Reaction equation

HRID 589368 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 (225 mg, 0.663 mmol) was dissolved in methanol (20 mL). 10% Pd/C(18 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, and 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-5880217a35b947ceb26a45746014af6d
Source dataset
uspto-grants-2016_01
Patent number
US09233098B2

Reaction notes

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