(5-Chloro-2-methoxypyridin-4-yl)boronic acid → 6-(5-Chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole

https://huagongshe.com/reaction/1944677

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	(5-Chloro-2-methoxypyridin-4-yl)boronic acid	HCID 11030558	—
Edukt	6-Bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole	HCID 59588803	—
Edukt	HCID 178476685	HCID 178476685	—
Katalysator	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Lösungsmittel	Dimethylformamide	HCID 6228	—
Produkt	6-(5-Chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole	HCID 23728892	6%

Reaktionsbedingungen

Temperatur	80 °C

Reaktionsschritte

To a solution of 6-bromo-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (500 mg, 1.48 mmol) and 5-chloro-2-methoxypyridin-4-yl-4-boronic acid (334 mg, 1.78 mmol) in DMF (20 mL) was added PdCl2(dppf) (108 mg, 0.148 mmol), followed by CH3COOK (581 mg, 5.92 mmol). The mixture was heated at 80° C. for 2 h, filtered and the volatiles evaporated. Water (5 mL) was added and the mixture was extracted with CH2Cl2 (3×5 mL). The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by the preparative HPLC to give 35 mg (6%) of 6-(5-chloro-2-methoxypyridin-4-yl)-2-(4-cyclopropylpiperazin-1-yl)benzothiazole as a trifluoroacetate salt.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08394842B2
Quelldatensatz	uspto-grants-2013_03
ORD ID	ord-f527a6e539aa43ec8b9cc303bf4025d2
Quellennotiz	uspto-grants-2013_03