2-Vinylpyridine → HCID 67199041, compound

HRID 547739Notes

Reaction equation

HRID 547739 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:22])[N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[C:13](Br)[CH:14]=1)#[N:2].[CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1)=[CH2:24].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:10](=[O:22])[N:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[C:13]([CH:24]=[CH:23][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[CH:14]=1)#[N:2]

Participants

7

Reactant 4

HCID 75212-VinylpyridineHCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 223189902-(5-Bromo-1,2-dihydro-2-oxo-1-phenyl-3-pyridinyl)benzonitrile

Product 1

HCID 67199041HCID 67199041, compoundYield 15%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixed liquid of 100 mg of 3-(2-cyanophenyl)-1-phenyl-5-bromo-1,2-dihydropyridin-2-one, 100 mg of 2-vinylpyridine, 6 mg of palladium acetate, 17 mg of tri-(o-tolyl)phosphine and 3 ml of triethylamine was stirred at 130° C. for 2 hours in nitrogen atmosphere. After cooling to room temperature, ethyl acetate was added thereto. The extract was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (ethyl acetate/hexane), to give 16 mg of the title compound as a white powder.

Workup

  1. washThe extract was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-42a1c4fdcf09430b98aa2403fda23365
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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