2-Vinylpyridine → HCID 59317767, compound

HRID 2067701Notes

Reaction equation

HRID 2067701 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=[CH2:12].[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:12][CH2:11][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 75212-VinylpyridineHCID 14798Sodium HydroxideHCID 249055-Bromoindole

Product 1

HCID 59317767HCID 59317767, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 5-bromoindole (5.9 g) in acetic acid (10 ml) solution, 2-vinylpyridine (3.6 ml) was added and the mixture was heated and refluxed for 15 hours. The reaction solution was cooled, then was diluted with ethyl acetate, the aqueous layer was made alkaline with 4N-aqueous sodium hydroxide solution and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off in vacuo, and the residue obtained was purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 17:33) to afford the above-identified compound (5.6 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 15 hours
  3. temperatureThe reaction solution was cooled
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. distillationthe solvent was distilled off in vacuo
  7. customthe residue obtained
  8. customwas purified by silica gel column chromatography (hexane:ethyl acetate=1:1 to 17:33)

Sources & evidence

ORD record
ord-2c6d4c00ecee4ba483428520ca794071
Source dataset
uspto-grants-2012_10
Patent number
US08293781B2

Reaction notes

Loading…