Dichloromethane → (2-Oxo-1,2-dihydroquinolin-3-yl)boronic acid

Participants

Role	Name	HCID	Charge
Reactant	Dichloromethane	HCID 6344	—
Reactant	Potassium Acetate	HCID 517044	—
Reactant	Bis(pinacolato)diborane	HCID 2733548	—
Reactant	HCID 178517115	HCID 178517115	—
Catalyst	Ferrocene-1,1'-bis-(diphenylphosphine)	HCID 635956	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	(2-Oxo-1,2-dihydroquinolin-3-yl)boronic acid	HCID 49757966	71.2%

Reaction Conditions

Temperature	90 °C

Reaction Steps

To a microwave vial was added 3-bromo-2-hydroxyquinoline (50 mg, 0.223 mmol), bis(pinacolato)diboron (113 mg, 0.446 mmol), potassium acetate (66 mg, 0.669 mmol), PdCl2(dppf). CH2Cl2 (18.22 mg, 0.022 mmol), and dppf (12.37 mg, 0.022 mmol), followed by addition of 1,4-dioxane (6 mL). The reaction mixture was purged with N2 and stirred under N2 atmosphere at 90° C. overnight. The reaction mixture was filtered through a disposable filter funnel, concentrated in vacuo, and purified by silica gel chromotography (10% to 60% EtOAc in heptane) to afford (2-oxo-1,2-dihydroquinolin-3-yl)boronic acid (30 mg, MS: 190.1 [M+H+].)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09040712B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-c2fb867fa4204514aa22184a3c521273
Source note	uspto-grants-2015_05