Potassium Carbonate → (3-Bromo-5-pyridin-3-yl-phenyl)-carbamic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	3-Pyridinylboronic acid	HCID 2734378	—
Reactant	(3-Bromo-5-iodo-phenyl)-carbamic acid methyl ester	HCID 68843615	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(3-Bromo-5-pyridin-3-yl-phenyl)-carbamic acid methyl ester	HCID 68843413	38.3%

Reaction Steps

(3-Bromo-5-iodo-phenyl)-carbamic acid methyl ester (0.22 g, 0.62 mmol), 3-pyridylboronic acid (0.11 g, 0.93 mmol), and Pd(dppf)Cl2.CH2Cl2 complex (0.051 g, 0.062 mmol) were dissolved in dioxane (6 mL). Aqueous 2 M potassium carbonate (0.26 g, 1.9 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr. The reaction mixture was then heated to 60° C. for 24 hrs. The reaction mixture was filtered through Celite® and the solvent was removed. The product was chromatographed to give 0.073 g (38% yield) of (3-bromo-5-pyridin-3-yl-phenyl)-carbamic acid methyl ester.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07504401B2
Source dataset	uspto-grants-2009_03
ORD ID	ord-0d665081fa7442c3a4216bae27b5bc2c
Source note	uspto-grants-2009_03