1,10-Phenanthroline → HCID 25118343, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-iodophenyl)-5-[5-methyl-1-(4-methylbenzyl)-1H-pyrazol-3-yl]-1,2,4-oxadiazole (Example 13, 200 mg, 0.44 mmol), 2-propanol (1 ml, 13.06 mmol), copper(I) iodide (8.4 mg, 0.04 mmol), phenanthroline (16 mg, 0.09 mmol) and cesium carbonate (286 mg, 0.88 mmol) was stirred at 100° C. for five hours in a microwave reactor (CEM Discover). The reaction mixture was cooled and water (50 mL) and ethyl acetate (50 mL) was added. The layers were separated and the organic layer was washed with water and brine and then dried with magnesium sulfate. The solvent was evaporated and the residue was purified using preparative HPLC to afford the title compound as a white solid (30 mg, 16%): 1H NMR (400 MHz, CDCl3) 8.12 (d, 2H), 7.13 (d, 2H), 7.07 (d, 2H), 6.97 (d, 2H), 6.79 (s, 1H), 5.41 (s, 2H), 4.63 (sept, 1H), 2.33 (s, 3H), 2.26 (s, 3H), 1.38 (d, 6H); ES-MS m/z 389 (MH)+, HPLC RT (Method E) 2.67 min.

Provenance & Evidence