Piperidine → 2-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethanol

Participants

Role	Name	HCID	Charge
Reactant	Piperidine	HCID 8082	—
Reactant	2-(4-Ethynylphenoxy)ethan-1-ol	HCID 18751415	—
Reactant	2-(4-Chlorophenyl)-5-iodopyrazine	HCID 85969636	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-{4-[5-(4-Chlorophenyl)pyrazin-2-ylethynyl]phenoxy}ethanol	HCID 69058814	—

Reaction Steps

Under an argon atmosphere 49 mg (0.06 mmol) of PdCl2(dppf) and 11 mg (0.06 mmol) of CuI were added to a repeatedly degassed solution of 535 mg (3.30 mmol) of 2-(4-chlorophenyl)-5-iodopyrazine, 950 mg (3.30 mmol) of 2-(4-ethynylphenoxy)ethanol, and 0.59 mL (6.00 mmol) of piperidine in 50 mL of THF and the mixture was stirred for 4 hours at RT. The precipitate was suction filtered and washed with acetonitrile. The mother liquor was concentrated, and the precipitate formed was filtered off and washed with acetonitrile. The precipitates were combined. Yield: 700 mg (67% of theoretical); C20H15ClN2O2 (M=350.798); calc.: molpeak (M+H)+:351/353 (Cl); found: molpeak (M+H)+:351/353 (Cl); Rf value: 0.30 (silica gel, PE/EtOAc 1:1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07592358B2
Source dataset	uspto-grants-2009_09
ORD ID	ord-ac501f2c3d544056a1bc86978d6f5c22
Source note	uspto-grants-2009_09