Sodium Iodide → N-(3((4-oxo-8-(3-(2-oxoindolin-1-yl)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide

Participants

Reaction Conditions

Reaction Steps

To a solution of N-(3((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)phenyl)methanesulfonamide (0.22 g, 0.53 mmol), sodium iodide (0.032 g, 0.21 mmol) and potassium carbonate (0.146 g, 1.06 mmol) in 2-butanone (5 mL), was added 1-(3-chloropropyl)indolin-2-one (0.11 g, 0.53 mmol). After stirring at 78° C. for 3 hours, the reaction mixture was filtered and isolated by preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.041 g, 13%); 1H NMR (DMSO-d6): δ 1.66 (d, 2H, J=13.6 Hz), 1.78 (t, 2H, J=6.8 Hz), 2.33-2.47 (m, 2H), 2.50-2.56 (m, 2H), 2.76 (br, 4H), 2.96 (s, 3H), 3.54 (s, 2H), 3.73 (t, 2H, J=6.8 Hz), 4.52 (s, 2H), 4.58 (s, 2H), 6.77 (t, 1H, J=7.2 Hz), 6.85 (d, 2H, J=8.4 Hz), 6.97-7.02 (m, 2H), 7.08-7.13 (m, 3H), 7.20-7.26 (m, 4H), 7.32 (t, 1H, J=8 Hz), 9.80 (s, 1H); MS for C32H37N5O4S m/z 588.3 (M+H)+.

Provenance & Evidence