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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1,1-Dimethylethyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate	HCID 4376766	—
Reactant	5-Bromo-8-morpholinoimidazo[1,2-a]pyrazine-2-carbaldehyde	HCID 117728113	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	tert-Butyl 4-(2-formyl-8-morpholinoimidazo[1,2-a]pyrazin-5-yl)benzoate	HCID 117733763	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249163B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-d61ac791e301454596f7dfe16c067364
Source note	uspto-grants-2016_02