Water → 5-(cyclohexylmethyl)-5-[4-(methylsulfonyl)phenyl]-5H-imidazo[2,1-a]isoindole

Participants

Reaction Steps

To a solution of 5-(cyclohexylmethyl)-5-[4-(methylthio)phenyl]-5H-imidazo[2,1-a]isoindole (38 mg) in MeOH (1 mL) was added water drop wise until the clear solution started to become turbid. Oxone (69 mg) was added at this time and stirred at room temperature 21 h. The reaction mixture was then diluted with MeOH, filtered and the filtrate was concentrated. Purification by reversed phase HPLC (21×100 mm Phenomenex Gemini, 15-85% MeCN/water containing 0.05% NH4OH over 20 min at 20 mL/min) afforded title compound as a white solid. HRMS. Found, 407.1802; calcd for (M+H)+, 407.1788. 1H NMR (500 MHz, CDCl3): δ 7.89-7.85 (m, 3 H); 7.45-7.39 (m, 1 H); 7.37 (d, J=1.28 Hz, 1 H); 7.32-7.26 (m, 3 H); 7.24 (d, J=8.00 Hz, 1 H); 6.99 (d, J=1.29 Hz, 1 H); 3.01 (s, 3 H); 2.60 (dd, J=14.41, 4.34 Hz, 1 H); 2.41 (dd, J=14.40, 4.00 Hz, 1 H); 1.54-1.38 (m, 3 H); 1.33-1.19 (m, 2 H); 1.10-0.73 (m, 7 H).

Provenance & Evidence