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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1497365Generated: October 27, 2026

Ammonia → 4-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

https://huagongshe.com/reaction/1497365

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantN,N'-DimethylethylenediamineHCID 8070—
ReactantPotassium CarbonateHCID 11430—
Reactant4-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 57497864—
Reactant5-bromo-2-cyclopropyl-3-methyl-2H-indazoleHCID 117798640—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
SolventDimethyl SulfoxideHCID 679—
Product4-[(4-chlorobenzyl)oxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-oneHCID 11779874438.9%

Reaction Steps

To a suspension of 5-bromo-2-cyclopropyl-3-methyl-2H-indazole (320 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (200 mg) and potassium carbonate (352 mg) in DMSO (20 ml) were added copper(I) iodide (162 mg) and N,N′-dimethylethylenediamine (112 mg), and the mixture was reacted at 150° C. for 1 hr under microwave irradiation. 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 (134 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09199963B2
Source datasetuspto-grants-2015_12
ORD IDord-b0d40714caf64cb086c2869e82d9931f
Source noteuspto-grants-2015_12