Pyrrolidine → (3E)-3-[1-(1H-indazol-6-yl)ethylidene]-1H-indol-2-one

Participants

Reaction Conditions

Reaction Steps

A solution of oxindole (16 mg, 0.12 mmol), pyrrolidine (10 μL, 0.12 mmol) and 1-(1H-indazol-6-yl)ethanone (20 mg, 0.12 mmol) in toluene was refluxed in a Dean-Stark trap for 2 h. The solution was then stirred at 50° C. for 72 h. Two equivalents of pyrrolidine were added and the solution was heated to reflux for 48 h. The solution was concentrated and the red residue was purified by preparatory HPLC to give the title compound as an orange solid (5 mg, 16%). 1H NMR (400 MHz, CDCl3) δ 8.13 (s, 1H), 7.78 (s, 1H), 7.70 (d, 1H, J=8.5 Hz), 7.34 (d, 1H, J=8.5 Hz), 7.03 (t, 1H, J=7.6 Hz), 6.81 (d, 1H, J=7.7 Hz), 6.50 (t, 1H, J=7.6 Hz), 6.05 (d, 1H, J=7.7 Hz), 2.82 (s, 3H); MS ESI [M+H]+, calcd for [C17H13N3O+H]+ 276.1; found m/z 276.0.

Provenance & Evidence