Sodium Carbonate → 2-Chloro-2'-fluoro-3,4'-bipyridine

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Tetrafluoroboric acid	HCID 28118	—
Reactant	Tris(1,1-dimethylethyl)phosphine	HCID 83681	—
Reactant	(2-Chloropyridin-3-yl)boronic acid	HCID 2762704	—
Reactant	2-Fluoro-4-iodopyridine	HCID 7023570	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Chloro-2'-fluoro-3,4'-bipyridine	HCID 16108982	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To 2-fluoro-4-iodopyridine (9.45 g, 42.4 mmol), 2-chloropyridine-3-boronic acid (10.0 g, 63.5 mmol), Na2CO3 (13.5 g, 127 mmol), Pd(OAc)2 (480 mg, 2.12 mmol) and P(tBu)3.HBF4 (1.23 g, 4.24 mmol) was added dioxane (125 mL) and water (45 mL). The mixture was heated overnight at 100° C. in a sealed tube. The resulting mixture was diluted with EtOAc and extracted with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The resulting solid was triturated with n-Hexanes and dried to yield 2-chloro-2′-fluoro-[3,4′]bipyridinyl. MS m/z=209 [M+1]+. Calc'd for C10H6ClFN2: 208.62.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08686155B2
Source dataset	uspto-grants-2014_04
ORD ID	ord-3699f47fba3940359518c90fd6788c82
Source note	uspto-grants-2014_04