Ammonia → 4-(benzyloxy)-1-(2-cyclopropyl-3-methyl-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-cyclopropyl-3-methyl-2H-indazole	HCID 117798640	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethyl Sulfoxide	HCID 679	—
Product	4-(benzyloxy)-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one	HCID 117798694	13.5%

Reaction Conditions

Temperature	150 °C

Reaction Steps

To a suspension of 5-bromo-2-cyclopropyl-3-methyl-2H-indazole (187 mg), 4-(benzyloxy)pyridin-2(1H)-one (100 mg) and potassium carbonate (206 mg) in DMSO (20 ml) were added copper(I) iodide (95 mg) and N,N′-dimethylethylenediamine (65.7 mg), and the mixture was stirred at 150° C. for 3 hr. The reaction mixture was added to 28% aqueous ammonia, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate/methanol) and recrystallized from ethyl acetate to give the title compound (25 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09199963B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-c597b7a367cf401aa963b1c5890ce45f
Source note	uspto-grants-2015_12