Potassium Carbonate → Methyl 3-(3-pyridinyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Bromopyridine	HCID 12286	—
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-(3-pyridinyl)benzoate	HCID 4133188	90%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (600 mg, 3.33 mmol), 3-bromopyridine (479 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 minutes with microwave heating under N2. The catalyst was then filtered and the filtrate concentrated. The residue was then purified by column chromatography to give the desired product and used directly in the next step. (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-1847187d0eac452281a98d3d17245484
Source note	uspto-grants-2015_03