2-Bromopyridine → 4-(2-Pyridyl)Benzoic Acid

Participants

Role	Name	HCID	Charge
Reactant	2-Bromopyridine	HCID 7973	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Carboxyphenylboronic Acid	HCID 312183	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	4-(2-Pyridyl)Benzoic Acid	HCID 821692	41.8%

Reaction Conditions

Temperature	125 °C

Reaction Steps

A mixture of 4-boronobenzoic acid (200 mg, 1.2 mmol), 2-bromopyridine (208 mg, 1.3 mmol), K2CO3 (497 mg, 3.6 mmol) and Pd(dppf)Cl2 (10 mg) in dioxane (4 mL) and H2O (1 mL) was stirred at 125° C. for 30 min with microwave heating under N2. The catalyst was filtered, and the filtrate was acidified with 2N HCl to pH 5˜6. The solution was concentrated, and the residue was dissolved in MeOH and filtered. The filtrate was concentrated, and the residue was purified by prep-TLC to give the title compound (100 mg, Yield 41.8%). LCMS (m/z): 200.1 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993555B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-9192a34332a441f49a4420f8f86f2171
Source note	uspto-grants-2015_03