Imidazole → HCID 59504680, compound

Participants

Reaction Steps

A suspension of 3-(4-iodophenyl)-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Example 13, 250 mg, 0.548 mmol), imidazole (56 mg, 0.822 mmol), caesium carbonate (197 mg, 0.603 mmol), copper-(I) trifluoromethanesulfonate (15 mg; 0.027 mmol), dibenzylideneacetone (6.7 mg, 0.027 mmol) and 1,10-phenanthroline (99 mg, 0.548 mmol) in toluene (1 mL) was heated to reflux under an inert atmosphere of argon over night. In order to increase solubility, DMF (100 μL) was added, and stirring was continued at 120° C. for 24 h. After being cooled to rt, water (5 mL) was added and the product was extracted with ethyl acetate. After the organic extract had been washed with brine and dried over anhydrous magnesium sulfate, it was filtered and concentrated in vacuo. The residue was subjected to preparative HPLC to afford the title compound in pure form (20 mg, 9%): 1H NMR (400 MHz, CDCl3) 8.33 (d, 2H), 7.98 (broad s, 1H), 7.53 (d, 2H), 7.38 (broad s, 1H), 7.26 (broad s, 1H, partially obscured by CHCl3 signal), 7.14 (d, 2H), 7.08 (d, 2H), 6.81 (s, 1H), 5.41 (s, 2H), 2.32 (s, 3H), 2.28 (s, 3H); ES-MS m/z 397, HPLC RT (Method K) 1.06 min.

Provenance & Evidence