Dimethylformamide → 1-Phenyl-3-(1-phenylacetylen-2-yl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Phenylacetylene	HCID 10821	—
Reactant	3-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one	HCID 22319065	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	1-Phenyl-3-(1-phenylacetylen-2-yl)-5-(2-pyridyl)-1,2-dihydropyridin-2-one	HCID 22318943	6.6%

Reaction Conditions

Temperature	50 °C

Reaction Steps

100 mg of 3-bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one, 55 mg of phenylacetylene, 1 mg of copper(I) iodide and 4 mg of dichlorobis(triphenylphosphine)palladium were added to a mixed solvent of 1.5 ml of triethylamine and 1 ml of dimethylformamide, and stirred at 50° C. in a nitrogen atmosphere for a night. The reaction mixture was distributed into the ethyl acetate and water layers. The organic layer was washed with water, dried and concentrated, and the residue was refined by silica gel chromatography (ethyl acetate/hexane-based solvent), to obtain 7 mg of the subject compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06949571B2
Source dataset	uspto-grants-2005_09
ORD ID	ord-90e291dac5434c5b9318a79ea19388e1
Source note	uspto-grants-2005_09