8-Hydroxyquinoline → 1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene

Participants

Role	Name	HCID	Charge
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2,5-Diiodofluorobenzene	HCID 2737096	—
Reactant	HCID 178516071	HCID 178516071	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Water	HCID 962	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene	HCID 59386661	—

Reaction Conditions

Temperature	130 °C

Reaction Steps

A mixture of 2,5-diiodofluorobenzene II-4 (2.00 g, 5.75 mmol), 2-hydroxypyridine 1-7 (0.546 g, 5.75 mmol), 8-hydroxyquinoline (0.083 g, 0.57 mmol) and K2CO3 (1.00 g, 7.25 mmol) in DMSO (10 mL) was degassed before being charged with CuI (0.109 g, 0.57 mmol). The mixture in a sealed tube was heated at 130° C. overnight. Water and EtOAc were added. The mixture was filtered. The organic layer was separated, then applied to a silica gel column, which was eluted with 0-70% EtOAc in hexane to give 1-iodo-2-fluoro-4-(2-oxopyridin-1(2H)-yl)benzene 3-2 (0.820 g). MS 315.8 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07767697B2
Source dataset	uspto-grants-2010_08
ORD ID	ord-68f11bc7a9454aa9b38a767126732b73
Source note	uspto-grants-2010_08