2-Bromopyridine → Methyl 3-(pyridin-2-yl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	2-Bromopyridine	HCID 7973	—
Reactant	Potassium Carbonate	HCID 11430	—
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-(pyridin-2-yl)benzoate	HCID 3364101	98.2%

Reaction Conditions

Temperature	120 °C

Reaction Steps

A mixture of (3-(methoxycarbonyl)phenyl)boronic acid (500 mg, 2.78 mmol), 2-bromopyridine (399 mg, 2.53 mmol), K2CO3 (1.0 g, 7.6 mmol) and Pd(dppf)Cl2 (20 mg) in a mixture solution of dioxane (10 mL) and H2O (2.5 mL) was stirred at 120° C. for 30 min under microwave heating. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by column chromatography to give the desired product (530 mg, Yield: 90%) and this was used directly in the next step. LCMS (m/z): 214.1.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993555B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-fd8fcdd3347c4cfa94ab5a1e66b8f8bf
Source note	uspto-grants-2015_03