Sodium Carbonate → HCID 59162019, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Bromo-5-fluoropyridine	HCID 2783171	—
Reactant	HCID 68668352	HCID 68668352	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 59162019	HCID 59162019	—

Reaction Conditions

Temperature	80 °C

Reaction Steps

Pd(dppf)Cl2 (579 mg, 0.7 mmol) was added to a degassed, ambient temperature solution of 1-[2,5-difluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (2 g, 7.1 mmol), 2-bromo-5-fluoropyridine (2.5 g, 14 mmol) and sodium carbonate (2.26 g, 21 mmol) in N,N-dimethyformamide (20 mL) and water (10 mL). After heating at 80° C. overnight, the reaction mixture was poured into water and extracted with diethyl ether. The combined organic phases were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08193228B2
Source dataset	uspto-grants-2012_06
ORD ID	ord-0e0c1606d9ff47bc9ba2ff6114ed77f6
Source note	uspto-grants-2012_06