HCID 22669595, compound → HCID 22669559, compound

HRID 1007475Notes

Reaction equation

HRID 1007475 reaction equation
[Cl: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][CH:9]=[C:8]2[CH:14]([CH3:16])[CH3:15]>C(O)C.[Pd]>[Cl:1][C:2]1[CH:20]=[C:19]([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][CH:9]=[C:8]2[CH:14]([CH3:15])[CH3:16])[NH2:21]

Participants

4

Reactant 1

HCID 22669595HCID 22669595, compound

Product 1

HCID 22669559HCID 22669559, compoundYield 59.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

500 mg of 5-(2-chloro-6-methyl-4-nitrophenoxy)-3-isopropyl-1H-indole (Example II) are suspended in 10 ml of ethanol and hydrogenated with 50 mg of palladium on active carbon (10%) at atmospheric pressure for 2 hours. The mixture is filtered through kieselguhr, the solvent is removed in vacuo and the product is purified by chromatography (cyclohexane/ethyl acetate). 271 mg of 3-chloro-4-[(3-isopropyl-1H-indol-5-yl)oxy]-5-methylaniline are obtained.

Workup

  1. filtrationThe mixture is filtered through kieselguhr
  2. customthe solvent is removed in vacuo
  3. customthe product is purified by chromatography (cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-297fd3bf9a594567a2f48d7c6dc4ddf6
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

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