Water → HCID 22319076, compound

HRID 497863Notes

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

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

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

Sources & evidence

ORD record: ord-b874e54052214bb4979c484b4947573d
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949571B2

Reaction notes

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