4-(3-Butyn-1-yl)benzenemethanol → (4-{4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-phenyl)-methanol

https://huagongshe.com/reaction/1916534

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	4-(3-Butyn-1-yl)benzenemethanol	HCID 23596609	—
Edukt	5-(4-Chlorophenyl)-2-iodopyridine	HCID 85969849	—
Katalysator	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Katalysator	HCID 178418476	HCID 178418476	—
Lösungsmittel	Methanol	HCID 887	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Lösungsmittel	Triethylamine	HCID 8471	—
Lösungsmittel	Ethyl Acetate	HCID 8857	—
Produkt	(4-{4-[5-(4-Chloro-phenyl)-pyridin-2-yl]-but-3-ynyl}-phenyl)-methanol	HCID 69071295	—

Reaktionsbedingungen

Temperatur	65 °C

Reaktionsschritte

Under a nitrogen atmosphere 76 mg (0.4 mmol) CuI and 281 mg (0.4 mmol) Pd(PPh3)2Cl2 are added to a solution of 1.27 g (7.92 mmol) (4-but-3-ynyl-phenyl)-methanol and 2.5 g (7.92 mmol) 5-(4-chloro-phenyl)-2-iodo-pyridine in 40 mL triethylamine and 20 mL DMF and the reaction mixture is stirred for 2 h at 65° C. The solvent is eliminated in vacuo, the residue is dissolved in a little EtOAc and MeOH and purified by chromatography on silica gel (gradient: cyc/EtOAc 3:1 to cyc/EtOAc 1:1).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08618132B2
Quelldatensatz	uspto-grants-2013_12
ORD ID	ord-b017d4da26884d0cb229c05bd861d94d
Quellennotiz	uspto-grants-2013_12