Sodium Carbonate → (R)-4-methyl-2-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)pentan-1-ol

https://huagongshe.com/de/reaction/1922239

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Sodium Carbonate	HCID 10340	—
Edukt	1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 2773987	—
Edukt	(R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)-4-methylpentan-1-ol	HCID 57725426	—
Katalysator	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Lösungsmittel	1,2-Dimethoxyethane	HCID 8071	—
Produkt	(R)-4-methyl-2-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)pentan-1-ol	HCID 57725516	32%

Reaktionsbedingungen

Temperatur	90 °C

Reaktionsschritte

To the reaction mixture of (R)-2-(6-(2-chloropyridin-4-yloxy)benzo[d]thiazol-2-ylamino)-4-methylpentan-1-ol (12 mg, 31 μmol) in 400 μL of DME, 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (21 mg, 100 μmol), Pd(dppf)2Cl2 (7 mg, 8 μmol) and aq. 2M Na2CO3 (100 μL, 200 μmol) were added. The reaction mixture was stirred at 90° C. for 24 hours. The reaction mixture filtered, purified on prep HPLC and evaporated in vacuo to give (R)-4-methyl-2-(6-(2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzo[d]thiazol-2-ylamino)pentan-1-ol as powder (4.2 mg). ES/MS m/z 424.1 (MH+).

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US08173689B2
Quelldatensatz	uspto-grants-2012_05
ORD ID	ord-8a5a17bdfa964a7583974430ca4bf693
Quellennotiz	uspto-grants-2012_05