Sodium Carbonate → 2-Chloro-3-(2-methoxypyridin-4-yl)pyridine

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	4-Iodo-2-methoxypyridine	HCID 15019795	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	2-Chloro-3-(2-methoxypyridin-4-yl)pyridine	HCID 58396653	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

To 4-iodo-2-methoxypyridine (834 mg, 3.55 mmol), 2-chloropyridine-3-boronic acid (838 mg, 5.32 mmol), Na2CO3 (1.13 g, 10.7 mmol), Pd(OAc)2 (40 mg, 0.18 mmol) and P(tBu)3.HBF4 (104 mg, 0.36 mmol) was added dioxane (12 mL) and water (4 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 MeOH and dried to yield the title compound. MS m/z=221 [M+1]+. Calc'd for C1lH9ClN2O: 220.66.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07880000B2
Source dataset	uspto-grants-2011_02
ORD ID	ord-9354e217929e412bb8358f067b529530
Source note	uspto-grants-2011_02