8-Hydroxyquinoline → 5-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	8-Hydroxyquinoline	HCID 1923	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	5-chloro-N-((1-(4-iodophenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamide	HCID 68502809	—
Reactant	HCID 178516071	HCID 178516071	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	5-Chloro-N-((1-(4-(2-oxopyridin-1(2H)-yl)phenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamide	HCID 59260076	18.1%

Reaction Conditions

Temperature	130 °C

Reaction Steps

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-pyrrol-3-yl)methyl)thiophene-2-carboxamide (118 mg, 0.27 mmol), 2-hydroxypyridine (50 mg, 0.53 mmol), 8-hydroxyquinoline (14 mg, 0.097 mmol) and K2CO3 (120 mg, 0.87 mmol) in DMSO (2 mL) was degassed with Argon before being charged with CuI (19 mg, 0.10 mmol). The mixture in a sealed tube was heated at 130° C. for 4 h. It was then purified by HPLC to give the titled compound (20 mg). MS 410.0 and 412.0 (M+H, Cl pattern).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07696352B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-5dbc56aa80f848dba2a388a30009b013
Source note	uspto-grants-2010_04