2-Bromopyridine → 2-(Pyridin-2-YL)benzoic acid

Participants

Role	Name	HCID	Charge
Reactant	2-Bromopyridine	HCID 7973	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-(Dihydroxyboranyl)benzoic acid	HCID 2733985	—
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	2-(Pyridin-2-YL)benzoic acid	HCID 15733175	42.9%

Reaction Conditions

Temperature	125 °C

Reaction Steps

A mixture of 2-boronobenzoic acid (400 mg, 2.4 mmol), 2-bromopyridine (416 mg, 2.6 mmol), K2CO3 (994 mg, 7.2 mmol) and Pd(dppf)Cl2 (20 mg) in dioxane (8 mL) and H2O (2 mL) was stirred at 125° C. for 30 min. under 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 (205 mg, Yield 42.9%). LCMS (m/z): 200.0 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08993555B2
Source dataset	uspto-grants-2015_03
ORD ID	ord-9c80a45b87834459a401f8590f85ee4e
Source note	uspto-grants-2015_03