N,N'-Dimethylethylenediamine → 2-(4-Chlorophenyl)-5-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)furo[3,2-c]pyridin-4(5H)-one

Participants

Role	Name	HCID	Charge
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-(4-chlorophenyl)-5H-furo[3,2-c]pyridine-4-one	HCID 58015558	—
Reactant	6-Bromo-2-cyclopropyl-1-methyl-1H-benzoimidazole	HCID 83825422	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	2-(4-Chlorophenyl)-5-(2-cyclopropyl-1-methyl-1H-benzimidazol-6-yl)furo[3,2-c]pyridin-4(5H)-one	HCID 117949622	22%

Reaction Conditions

Temperature	190 °C

Reaction Steps

A mixture of 2-(4-chlorophenyl)furo[3,2-c]pyridin-4(5H)-one (100 mg), 6-bromo-2-cyclopropyl-1-methyl-1H-benzimidazole (123 mg), N,N′-dimethylethylenediamine (0.043 mL), copper(I) iodide (78.0 mg), potassium carbonate (169 mg) and DMSO (3.0 mL) was stirred at 190° C. for 1 hr under microwave irradiation. The reaction mixture was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and the obtained solid was washed with ethyl acetate to give the title compound (37.3 mg) as a pale red solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09440987B2
Source dataset	uspto-grants-2016_09
ORD ID	ord-0d33230c536c4ac384f6fa866e11d8a8
Source note	uspto-grants-2016_09