Cesium carbonate → 3-(2-Cyanophenyl)-1-(2-pyridyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one

HRID 229671Notes

Reaction equation

HRID 229671 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=[C:9](Br)[C:8]1=[O:20].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B1OC(C([O-])=O)C=CO1)#[N:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:9]1[C:8](=[O:20])[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:10]=1)#[N:22]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 223190411-(2-Pyridyl)-5-(2-pyridyl)-3-bromo-1,2-dihydropyridin-2-oneHCID 865903732-(2-Cyanophenyl)-1,3,2-dioxaborinate

Product 1

HCID 223191183-(2-Cyanophenyl)-1-(2-pyridyl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.05 g of 1-(2-pyridyl)-5-(2-pyridyl)-3-bromo-1,2-dihydropyridin-2-one, 0.04 g of 2-(2-cyanophenyl)-1,3,2-dioxaborinate, 0.02 g of tetrakistriphenylphosphine palladium and 0.1 g of cesium carbonate was stirred at 120° C. in a nitrogen atmosphere for 2 hours in dimethylformamide. The mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and then saturated saline water, and dried by magnesium sulfate anhydride. The solvent was concentrated under a vacuum, and the residue was refined by silica gel chromatography (ethyl acetate/hexane=3:1), to obtain 0.04 g of the white, powdery subject compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialsaturated saline water, and dried by magnesium sulfate anhydride
  4. concentrationThe solvent was concentrated under a vacuum
  5. customto obtain 0.04 g of the white, powdery subject compound

Sources & evidence

ORD record
ord-8a2d7f89ebda42a0aa830e4ff3fb3481
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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