Water → 5-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]pent-3-yn-2-one

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Acetyl chloride	HCID 6367	—
Reactant	Triethylamine	HCID 8471	—
Reactant	3-Nitro-2-(4-prop-2-ynylidenepiperidin-1-yl)pyridine	HCID 86627335	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	5-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]pent-3-yn-2-one	HCID 25181792	28.8%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of Compound 1c (52 mg; 0.213 mmol), acetyl chloride (46 mL, 0.647 mmol), bis(triphenyl)palladium(II)dichloride (4.49 mg, 0.0064 mmol) and copper (I) iodide (1.62 mg, 0.085 mmol) in anhydrous THF (5 mL), was added triethylamine (85 μL, 0.61 mmol) and the reaction mixture was stirred, in a closed vessel, at 60° C. for 5 h, cooled to r.t. poured into water and extracted with EtOAc. The combined extracts were washed with NaOH 0.1N, water, dried over Na2SO4 and evaporated to dryness in vacuo. Purification by flash chromatography (EtOAc—Petroleum Ether 25:75), afforded 17.5 mg of the title product.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08518916B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-b52bbee1dcd24fabb5ffce112be5913d
Source note	uspto-grants-2013_08