Ammonia → 4-[(4-Chlorophenyl)methoxy]-1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-2(1H)-pyridinone

Participants

Reaction Conditions

Reaction Steps

Then a mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (1.0 g), 2-cyclopropyl-6-iodo-3-methylimidazo[1,2-a]pyridine (1.27 g), N,N′-dimethylethylenediamine (0.48 ml), copper iodide (0.81 g), potassium carbonate (1.76 g) and DMSO (13 ml) was heated at 110° C. under microwave irradiation for 1 h. Other two batches using 200 mg and 1 g of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one were conducted. Then these reaction mixtures were combined, and poured into 14% NH3 solution. The mixture was extracted with 1:1 mixture of EtOAc and THF. The extract was washed with brine, dried over MgSO4, concentrated, and purified by silica gel column chromatography (hexane/EtOAc then EtOAc/MeOH), followed by NH silica gel column chromatography (hexane/EtOAc) to give the title compound as a white solid (950 mg).

Provenance & Evidence