1,1'-Thiocarbonyldiimidazole → 3-((E)-4-((E)-2-Phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)styryl)-1,2,4-oxadiazole-5(4H)-thione

Participants

Reaction Steps

To a solution of (1Z,2E)-N′-hydroxy-3-(4-((E)-2-phenyl-1-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-yl)but-1-en-1-yl)phenyl)acrylimidamide (90 mg, 0.18 mmol; Compound 435, Step 2) and thiocarbonyldiimidazole (50 mg, 0.28 mmol) in anhydrous acetonitrile (1.5 mL) was added DBU (0.11 mL, 0.72 mmol). The solution was stirred at room temperature for 4 h then directly concentrated onto silica gel. Purification by column chromatography (0 to 80% EtOAc/hexanes) afforded 69 mg of the title compound as an orange oil. LCMS: 451 [(M-THP+H)+H]+.

Provenance & Evidence