Ammonia → 4-(benzyloxy)-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	N,N'-Dimethylethylenediamine	HCID 8070	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	4-Benzyloxy-2(1H)-pyridone	HCID 3607724	—
Reactant	5-bromo-2,3-dimethyl-2H-indazole	HCID 11499567	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	4-(benzyloxy)-1-(2,3-dimethyl-2H-indazol-5-yl)pyridin-2(1H)-one	HCID 117816803	65.3%

Reaction Conditions

Temperature	150 °C

Reaction Steps

A suspension of 5-bromo-2,3-dimethyl-2H-indazole (1.85 g), 4-(benzyloxy)pyridin-2(1H)-one (1.65 g), potassium carbonate (3.41 g), copper(I) iodide (1.57 g) and N,N′-dimethylethylenediamine (0.73 g) in DMSO (30 ml) was stirred at 150° C. for 3 hr. The reaction mixture was cooled to room temperature, and added to 28% aqueous ammonia, and the obtained precipitates were collected by filtration. The obtained solid was washed with water and diisopropyl ether, and dried under reduced pressure to give the title compound (1.85 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09199963B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-74c313ec6f764a3b8058f3700090c7b2
Source note	uspto-grants-2015_12