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 44119782	—
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 (100.0 mg, 0.320 mmol), 4-(tert-butoxycarbonyl)benzeneboronic acid pinacol ester (117 mg, 0.390 mmol), dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloromethane adduct (24.0 mg, 0.0320 mmol), and 1M sodium carbonate (1.61 mL, 1.61 mmol) in dioxane (6 mL) was purged with Argon gas. The resulting mixture was heated to 80° C. for 18 h. After the mixture was cooled, it was filtered through a pad of diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue was purified by Preparative TLC (EtOAc/CH2Cl2; 2:3, v/v) to give compound 81a. Mass Spectrum (LCMS, ESI pos.): Calcd. for C22H25N4O4: 409.2 (M+H). found: 409.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09249163B2
Source dataset	uspto-grants-2016_02
ORD ID	ord-249d72cb477a4bef830b291be3e58507
Source note	uspto-grants-2016_02