Sodium Carbonate → tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Sodium Carbonate	HCID 10340	—
Edukt	1,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate	HCID 4376766	—
Edukt	5-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehyde	HCID 117728113	—
Katalysator	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Lösungsmittel	1,4-Dioxane	HCID 31275	—
Produkt	tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate	HCID 117733763	—

Reaktionsbedingungen

Temperatur	80 °C

Reaktionsschritte

A mixture of compound 2a (1.0 g, 3.2 mmol), 4-(tert-butoxycarbonyl)phenylboronic acid pinacol ester (1.2 g, 3.9 mmol), PdCl2(dppf) (260 mg, 0.30 mmol), 2M Na2CO3 (8.0 mL, 16 mmol) in dioxane (10 mL) was heated to 80° C. for 2 h. The reaction was cooled, filtered through a diatomaceous earth-filled cartridge (2.5 g), and the filter cake was rinsed with EtOAc. The combined filtrates were concentrated under reduced pressure. The residue was diluted with DCM and extracted with water, brine, then dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was triturated with MeOH, filtered and dried to give compound 67a. Mass Spectrum (LCMS, ESI pos.) Calcd. for C22H24N4O4: 409.4 [M+H]. found 409.4.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US09249163B2
Quelldatensatz	uspto-grants-2016_02
ORD ID	ord-d61ac791e301454596f7dfe16c067364
Quellennotiz	uspto-grants-2016_02