Morpholine → HCID 25118344, 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), morpholine (76 μl, 0.88 mmol), potassium carbonate (121 mg, 0.88 mmol), tris(dibenzylideneacetone)dipalladium (13 mg, 0.014 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′-tri-tert-butyl-1,1′-biphenyl (21 mg 0.044 mmol), DMF (1 ml) and tert-butanol (4 ml) was stirred at 80° C. for 15 h. The reaction mixture was cooled and water (100 mL) and ethyl acetate (100 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, first using preparative HPLC, then via flash chromatography (silica, cyclohexane/ethyl acetate, 10:1→2:1) to afford the title compound as a white solid (37 mg, 20%): 1H NMR (400 MHz, CDCl3) 8.11 (d, 2H), 7.13 (d, 2H), 7.07 (d, 2H), 6.97 (d, 2H), 6.78 (s, 1H), 5.41 (s, 2H), 3.88 (m, 4H), 3.28 (m, 4H), 2.33 (s, 3H), 2.25 (s, 3H); ES-MS m/z 416 (MH)+, HPLC RT (Method D) 2.95 min.

Provenance & Evidence