Water → HCID 22319076, compound

HRID 229700Notes

Reaction equation

HRID 229700 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:26])[N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:13]=2)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](B(CC)CC)[CH3:34].O>CN(C)C=O>[CH2:33]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:26])[N:10]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=3)[CH:13]=2)=[CH:4][N:3]=1)[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 7357TriethylboraneHCID 11430Potassium CarbonateHCID 22318983HCID 22318983, compound

Product 1

HCID 22319076HCID 22319076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

13 mg of 3-(2-chloropyridin-5-yl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one was dissolved in 20 ml of dimethylformamide, followed by the addition of 10 mg of potassium carbonate and 2 mg of tetrakistriphenylphosphine palladium. Under stirring at room temperature in nitrogen atmosphere, triethylborane (1.0M tetrahydrofuran solution) was added dropwise thereinto, followed by heating under stirring at 100° C. for 1 hour in nitrogen atmosphere. After the reaction mixture was cooled to room temperature, water was added thereto, and extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel chromatography (hexane/ethyl acetate system), to give 4 mg of the title compound.

Workup

  1. additionwas added dropwise
  2. temperatureby heating
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-e7e6f810091f41f1b47dbe00922fdbc4
Source dataset
uspto-grants-2009_07
Patent number
US07563811B2

Reaction notes

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