5-Bromonicotinonitrile → Tert-butyl 4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	5-Bromonicotinonitrile	HCID 736793	—
Reactant	tert-Butyl 4-(prop-2-yn-1-ylidene)piperidine-1-carboxylate	HCID 86661548	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Product	Tert-butyl 4-[3-(5-cyanopyridin-3-yl)prop-2-ynylidene]piperidine-1-carboxylate	HCID 25183829	100%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of Compound 2b (0.5 g, 2.26 mmol), 5-bromonicotinonitrile (0.511 g, 2.26 mmol), bis(triphenylphosphine)palladium(II)dichloride (80 mg, 0.05 mmol), CuI (43.1 mg, 0.1 mmol) in anhydrous and degassed triethylamine (12.6 mL) was heated at 80° C. under a nitrogen atmosphere for 2 h in a sealed vessel. The reaction mixture was cooled, filtered on Celite, poured into water and extracted with EtOAc. The combined organic layers were washed with brine, dried on Na2SO4 and evaporated to dryness in vacuo to afford a residue, which was purified by flash chromatography (EtOAc—Petroleum Ether gradient from 4:96 to 30:70) affording the title product (0.731 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08518916B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-42c85cdf19894ecebce7f923b5165288
Source note	uspto-grants-2013_08