3-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole → 4-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylaniline

HRID 1007485Notes

Reaction equation

HRID 1007485 reaction equation
[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:19]([CH3:20])=[CH:18][C:17]([N+:21]([O-])=O)=[CH:16][C:15]=3[CH3:24])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]>CO.C(O)C.[Pd]>[CH:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][C:14]3[C:15]([CH3:24])=[CH:16][C:17]([NH2:21])=[CH:18][C:19]=3[CH3:20])[CH:11]=2)[NH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 226695113-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

Product 1

HCID 226697004-[(3-isopropyl-1H-indol-5-yl)oxy]-3,5-dimethylaniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18681192Ethanol, mixt. with methanolSolvent

Procedure

11.95 g (36.85 mmol) of nitro compound from Example XIV are hydrogenated in 500 ml of methanol/ethanol mixture using 550 mg of palladium/active carbon (10%) at 3 bar. The mixture is filtered through kieselguhr, the solvent is removed in vacuo and the product is purified by chromatography (toluene/ethyl acetate).

Workup

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

Sources & evidence

ORD record
ord-b93b70a43e424661ae7e9e9f27340605
Source dataset
uspto-grants-2004_09
Patent number
US06794406B2

Reaction notes

Loading…