N,N'-Dimethylethylenediamine → 1-(3-tert-butyl-5-iodo-4-methoxyphenyl)pyridin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

In a 20 mL microwave tube were added pyridin-2-ol (190 mg, 2 mmol), copper(I) iodide (76 mg, 0.400 mmol), 1-tert-butyl-3,5-diiodo-2-methoxybenzene (998 mg, 2.400 mmol), potassium phosphate (849 mg, 4.00 mmol) and N,N′-dimethylethylenediamine (0.086 mL, 0.800 mmol) in dioxane (10 mL). The tube was sealed and the mixture was sparged with N2 for 10 minutes and heated in an oil bath at 110° C. for 16 hours. The mixture was cooled and partitioned into ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, dried (Na2SO4), filtered and the filtrate was treated with 3-mercaptopropyl functionalized silica gel, filtered through diatomaceous earth and concentrated in vacuo to give crude product which was purified on an Isco 12 g silica cartridge eluting with 3:2 hexane/ethyl acetate to give the title compound.

Provenance & Evidence