Sodium Carbonate → HCID 66678170, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Amino-6-bromo-N-pyridin-3-ylpyrazine-2-carboxamide	HCID 10402162	—
Reactant	(3-Methoxy-propyl)-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl-carbamic acid tert-butyl ester	HCID 58065590	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 66678170	HCID 66678170	—

Reaction Steps

A mixture of the product of step (iv) (250 g, 0.58 mol), 3-amino-6-bromo-N-(pyridin-3-yl)pyrazine-2-carboxamide (220 g, 0.75 mol), Na2CO3 (183 g, 1.73 mol) and Pd(dppf)Cl2 (25.30 g, 35 mmol) in DMF (3 L) was stirred and degassed with N2 three times. The mixture was stirred at 70˜80° C. under N2 for 24 hours. The mixture was filtered and the filtrate concentrated to in vacuo to remove DMF. EtOAc (1.5 L) and H2O (800 mL) were charged and stirred for 1 hour at 10-25° C. The suspension was filtered, the organic phase was concentrated in vacuo and purified by column chromatography (PE: EtOAc=3:1-1:3). The crude product was re-crystallized from EtOAc-MeOH and filtered, the yellow solid was washed by EtOA and dried under reduced pressure. The subtitle compound (v) was obtained (pale yellow solid, 160 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08198285B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-944616c7422747fdad1ab242d2595849
Source note	uspto-grants-2012_06