HCID 178428762, compound → 5-(4-amino-2,6-dimethylphenoxy)-3-isopropyl-1H-indazole

HRID 396137Notes

Reaction equation

HRID 396137 reaction equation
[CH3:1][C:2]1[CH:20]=[C:19]([N+:21]([O-])=O)[CH:18]=[C:17]([CH3:24])[C:3]=1[O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH:14]([CH3:16])[CH3:15]>C(O)C.[Pd]>[NH2:21][C:19]1[CH:20]=[C:2]([CH3:1])[C:3]([O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[NH:10][N:9]=[C:8]3[CH:14]([CH3:15])[CH3:16])=[C:17]([CH3:24])[CH:18]=1

Participants

4

Reactant 1

HCID 178428762HCID 178428762, compound

Product 1

HCID 1784285015-(4-amino-2,6-dimethylphenoxy)-3-isopropyl-1H-indazoleYield 31.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

25 mg of palladium/carbon (10%) are suspended in a solution of 175 mg (0.538 mmol) of 5-(2,6-dimethyl-4-nitrophenoxy)-3-isopropyl-1H-indazole in 10 ml of ethanol. The mixture is shaken under a hydrogen atmosphere at 3 bar for 4 h, then filtered off through kieselguhr, the filtrate is concentrated in vacuo and the residue is purified on silica gel (cyclohexane/ethyl acetate 2:1). 50 mg (31%) of 5-(4-amino-2,6-dimethylphenoxy)-3-isopropyl-1H-indazole are obtained.

Workup

  1. filtrationfiltered off through kieselguhr
  2. concentrationthe filtrate is concentrated in vacuo
  3. customthe residue is purified on silica gel (cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-01acd732c89f458d9fb51081c87699f1
Source dataset
uspto-grants-2003_08
Patent number
US06608049B2

Reaction notes

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