Picolinic acid → 1-(2,6-diisopropylphenyl)-2-(3-(3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-5-methylphenoxy)phenyl)-1H-imidazole

Participants

Reaction Conditions

Reaction Steps

To a 300 mL 3-neck round bottom flask was added 3-(1-(2,6-diisopropylphenyl)-1H-imidazol-2-yl)-5-methylphenol (2.5 g, 7.47 mmol), 2-(3-bromophenyl)-1-(2,6-diisopropylphenyl)-1H-imidazole (3.15 g, 8.22 mmol), picolinic acid (1.380 g, 11.21 mmol), copper(I) iodide (0.427 g, 2.242 mmol), potassium phosphate tribasic monohydrate (6.02 g, 26.2 mmol), 100 mL DMSO. Nitrogen was bubbled directly into the mixture and then was heated to 200° C. overnight under nitrogen. The reaction mixture was diluted with ethyl acetate and water and was filtered through Celite. The layers were separated and the aqueous layer was extracted with ethyl acetate. The organic layers were washed with 10% LiCl, brine, dried over magnesium sulfate, filtered, and evaporated leaving a residue. The residue was purified by column chromatography eluting with 40 and 50% ethyl acetate/hexane (1.95 g, 41%).

Provenance & Evidence