Sodium Carbonate → HCID 59161939, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-Bromo-5-fluoropyridine	HCID 2783171	—
Reactant	1022154-90-0	HCID 86638490	—
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 59161939	HCID 59161939	—

Reaction Conditions

Temperature	90 °C

Reaction Steps

Pd(dppf)Cl2 (3.06 g, 4.2 mmol) was added to a degassed, ambient temperature solution of 2,2-difluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanone (30 g, 84 mmol), 2-bromo-5-fluoropyridine (15 g, 84 mmol) and sodium carbonate (20 g, 189 mmol) in N,N-dimethylformamide (400 mL) and H2O (100 mL). After stirring at 90° C. overnight, the reaction mixture was poured into ice and extracted with diethyl ether. The combined organic extracts were dried (magnesium sulfate), filtered and concentrated in vacuo. Chromatography over silica eluting with petroleum ether/ethyl acetate (20:1) 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-54e886e50d2b4c25a568e3c72414680c
Source note	uspto-grants-2012_06