4-Bromo-2-nitroaniline → tert-butyl 4-(4-amino-3-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate

https://huagongshe.com/de/reaction/58140

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	4-Bromo-2-nitroaniline	HCID 70132	—
Edukt	Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate	HCID 4642098	—
Edukt	Tripotassium phosphate trihydrate	HCID 18407952	—
Katalysator	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Lösungsmittel	Water	HCID 962	—
Lösungsmittel	1,4-Dioxane	HCID 31275	—
Produkt	tert-butyl 4-(4-amino-3-nitrophenyl)-5,6-dihydropyridine-1(2H)-carboxylate	HCID 59843222	75%

Reaktionsbedingungen

Temperatur	110 °C

Reaktionsschritte

To a degassed mixture of 4-bromo-2-nitroaniline (1 g, 4.6 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.42 g, 4.6 mmol), tripotassium phosphate trihydrate (3.9 g, 14.64 mmol) in dioxane and water (30 mL, 8:1) was added Pd(dppf)2Cl2 (337 g, 0.46 mmol). The mixture was refluxed at 110° C. for 3 hours. Filtration and concentration gave crude product, which was purified by silica gel column chromatography to afford the title compound (1.1 g, yield: 75%). MS (ESI): 320 [M+H]+.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09434697B2
Quelldatensatz	uspto-grants-2016_09
ORD ID	ord-413bdf926a4947f88b057a03eb098fee
Quellennotiz	uspto-grants-2016_09