2-Vinylpyridine → HCID 67199350, compound

HRID 547721Notes

Reaction equation

HRID 547721 reaction equation
Br[C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C.[CH:50]([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][N:53]=1)=[CH2:51]>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[N:53]1[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=1[CH:50]=[CH:51][C:2]1[C:3](=[O:20])[N:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 75212-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 223190653-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one

Product 1

HCID 67199350HCID 67199350, compoundYield 8.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

23 mg of 3-bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 20 ml of acetonitrile. To the mixture were added 0.2 mg of palladium acetate, 4.3 mg of tri-o-tolylphosphine and 0.04 ml of triethylamine, followed by stirring at 110° C. in nitrogen atmosphere overnight. To the mixture was added 9.2 mg of 2-vinylpyridine, followed by stirring at 110° C. in nitrogen atmosphere for 5 hours. After cooling to room temperature, the reaction mixture was poured into water, followed by extracting with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 2 mg of the title compound.

Workup

  1. stirringby stirring at 110° C. in nitrogen atmosphere for 5 hours
  2. temperatureAfter cooling to room temperature
  3. extractionby extracting with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-4408c712c04f49c2af114f3346d854ff
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

Loading…