1,2-Dibromoethane → HCID 58960089, compound

HRID 916153Notes

Reaction equation

HRID 916153 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5](=[O:30])[CH:6]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[Br:31][CH2:32][CH2:33]Br>C(O)C>[CH3:3][O:4][C:5](=[O:30])[CH:6]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[N:25][CH:24]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:33][CH2:32][Br:31])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 14797Potassium HydroxideHCID 58960088HCID 58960088, compound

Product 1

HCID 58960089HCID 58960089, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (0.17 g, 2.95 mmol) in ethanol (20 ml) is added 2-((2-nicotinoylphenyl)amino)-3-(4-hydroxyphenyl)-propionic acid methyl ester (1.10 g, 2.95 mmol) and 1,2-dibromoethane (5.54 g, 29.50 mmol). Then the mixture is heated to reflux for 8 hours. After cooled, the reaction mixture is filtered to remove the solid formed, and then the filtrate is evaporated under a vacuum. The crude product is purified by silica gel chromatography using hexane/EtOAc (4:1) as eluent to give the title compound (0.40 g, 28.2%).

Workup

  1. temperatureThen the mixture is heated
  2. temperatureto reflux for 8 hours
  3. temperatureAfter cooled
  4. filtrationthe reaction mixture is filtered
  5. customto remove the solid
  6. customformed
  7. customthe filtrate is evaporated under a vacuum
  8. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-26fbfe4d24214600bdb1e8bb67d12fc0
Source dataset
uspto-grants-2007_09
Patent number
US07268157B2

Reaction notes

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