8-Hydroxyquinoline → HCID 67072314, compound

Participants

Role	Name	HCID	Charge
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	1-Bromo-4-(methylsulphonyl)benzene	HCID 77014	—
Reactant	4-Benzyloxy-2(1H)-pyridone	HCID 3607724	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Solvent	Ethyl Acetate	HCID 8857	—
Solvent	Ammonium Hydroxide	HCID 14923	—
Product	HCID 67072314	HCID 67072314	66%

Reaction Conditions

Temperature	145 °C

Reaction Steps

A mixture of 4-benzyloxy-2(1H)-pyridone (6.87 g, 34.1 mmol, Aldrich), 4-bromophenyl methyl sulphone (8.01 g, 34.1 mmol, Combi-Blocks Inc.), copper(I) iodide (1.30 g, 6.82 mmol, Aldrich), 8-hydroxyquinoline (0.99 g, 6.82 mmol, Alfa Aesar) and potassium carbonate (6.12 g, 44.3 mmol, EMD) in DMSO (100 mL) was heated at 145° C. for 6 h, cooled to room temperature and then diluted with 10% NH4OH aqueous solution (50 mL) and EtOAc (100 mL). The resulting mixture was filtered and the solid was washed with H2O and EtOAc to give 8.0 g crude product as a greenish solid. MS (ESI) 356 (M+H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08372837B2
Source dataset	uspto-grants-2013_02
ORD ID	ord-a61cdbcaeae24d89910e68ac8fca999c
Source note	uspto-grants-2013_02