N-(5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide → N-(5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide

HRID 1107966Notes

Reaction equation

HRID 1107966 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8]([CH3:24])=[C:9]2[C:13](=[C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]=1[CH3:16])[NH:12][CH2:11][CH2:10]2)=[O:5])[CH3:2]>C1(C)C(C)=CC=CC=1.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8]([CH3:24])=[C:9]2[C:13](=[C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22])[C:15]=1[CH3:16])[NH:12][CH:11]=[CH:10]2)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 12112203N-(5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 22247308N-(5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamideYield 90.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7237O-XyleneSolvent

Procedure

N-(5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (1.0 g) was dissolved in xylene (75 ml), and 10% Pd-C (250 mg) was added, which was followed by refluxing for 1 hr. Pd-C was filtered off and xylene was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: benzene-CHCl3) to give 0.9 g of N-(5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide.

Workup

  1. temperatureby refluxing for 1 hr
  2. filtrationPd-C was filtered off
  3. customxylene was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: benzene-CHCl3)

Sources & evidence

ORD record
ord-1d9df4407bf2481f8a35aab606591f5e
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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