4-Bromo-2,6-difluoroanisole → 2-(4-(3-(3,5-Difluoro-4-methoxyphenyl)prop-2-yn-1-ylidene)piperidin-1-yl)-3-nitropyridine

Participants

Role	Name	HCID	Charge
Reactant	4-Bromo-2,6-difluoroanisole	HCID 2773287	—
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	—
Catalyst	Dichlorobis(triphenylphosphine)palladium	HCID 6102075	—
Product	2-(4-(3-(3,5-Difluoro-4-methoxyphenyl)prop-2-yn-1-ylidene)piperidin-1-yl)-3-nitropyridine	HCID 86627339	27.7%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of Compound 1c (50 mg, 0.206 mmol), 4-bromo-2,6-difluoroanisole (45.9 mL, 0.206 mmol), bis(triphenylphosphine)palladium(II)dichloride (7.23 mg, 0.012 mmol), CuI (3.92 mg, 0.206 mmol) in anhydrous and degassed triethylamine (3 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 10:90) affording the title product (22 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08518916B2
Source dataset	uspto-grants-2013_08
ORD ID	ord-fc3d88a971a54ff5addcf22fcd08caeb
Source note	uspto-grants-2013_08