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

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-bromo-2,3-dimethyl-2H-indazole (287 mg), 4-[(4-chlorobenzyl)oxy]pyridin-2(1H)-one (300 mg), potassium carbonate (528 m g), copper(I) iodide (242 mg) and N,N′-dimethylethylenediamine (112 mg) in DMSO (10 ml) was stirred at 150° C. for 3 hr. The reaction mixture was cooled to room temperature, added to 28% aqueous ammonia, and extracted with a 1:1 mixed solvent of ethyl acetate and tetrahydrofuran. 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) to give the title compound (150 mg).

Provenance & Evidence