Potassium Carbonate → Methyl 3-(4-pyridyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Bromopyridine	HCID 14268	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	3-(Methoxycarbonyl)benzeneboronic acid	HCID 2734714	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Product	Methyl 3-(4-pyridyl)benzoate	HCID 5152687	98.5%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (600 mg, 3.33 mmol), 4-bromopyridine (583.5 mg, 3.0 mmol), K2CO3 (1.2 g, 9.0 mmol) and Pd(dppf)Cl2 (50 mg) in a solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 min with microwave heating. The catalyst was filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the title product (630 mg Yield 90%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993555B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-0d5b609796d5498da36237ae9c0f9c11
Source note	uspto-grants-2015_03