HCID 10814436, compound → HCID 22645668, compound

HRID 2186697Notes

Reaction equation

HRID 2186697 reaction equation
Br[C:2]1[C:3](=[O:31])[N:4]([CH3:30])[C:5](=[O:29])[C:6]=1[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1[NH:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2>CO.[OH-].[OH-].[Pd+2]>[NH:21]1[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:28]=[C:20]1[CH2:19][CH2:18][CH2:17][CH2:16][C:8]1[NH:9][C:10]2[C:15]([C:7]=1[CH:6]1[CH2:2][C:3](=[O:31])[N:4]([CH3:30])[C:5]1=[O:29])=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

4

Reactant 1

HCID 10814436HCID 10814436, compound

Product 1

HCID 22645668HCID 22645668, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 240 mg (0.50 mmol) of 3-bromo-4-(2-(4-(1H-2-indolyl)butyl)-1H-3-indolyl)-1-methyl-2,5-dihydro-1H-pyrrole-2,5-dione and 140 mg (0.25 mmol) of Pd(OH)2/C (20%) in 30 ml of MeOH is stirred under an H2 atmosphere at room temperature for 24 h. For work-up, the mixture is filtered, the filtrate is concentrated and the residue is purified by column chromatography (SiO2:CH2Cl2/EA 95:5). On concentrating the pure fraction, the product is crystallized by addition of PE. Yield: 48.0 mg (24%), beige powder

Workup

  1. filtrationFor work-up, the mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customthe residue is purified by column chromatography (SiO2:CH2Cl2/EA 95:5)
  4. concentrationOn concentrating the pure fraction
  5. customthe product is crystallized by addition of PE

Sources & evidence

ORD record
ord-85aadf89ad2840bc8013736288ce0cb7
Source dataset
uspto-grants-2002_06
Patent number
US06407102B1

Reaction notes

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