Sodium Iodide → Tert-butyl 2-((8-(3-(3-fluoro-3-methyl-2-oxoindolin-1-yl)propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.17 g, 0.4 mmol), sodium iodide (0.018 g, 0.12 mmol) and potassium carbonate (0.083 g, 0.6 mmol) in 2-butanone (4 mL), was added 1-(3-chloropropyl)-3-fluoro-3-methylindolin-2-one (0.097 g, 0.4 mmol). After stirring at 78° C. for 5 hours, the reaction mixture was filtered and isolated by Biotage flash chromatography (1-10% methanol/dichloromethane) to obtain the title compound (0.11 g, 44%); 1H NMR (DMSO-d6): δ 1.57 (s, 9H), 1.65-1.72 (m, 5H), 1.79 (t, 2H, J=6.8 Hz), 2.35 (t, 2H, J=6.4 Hz), 2.56-2.71 (m, 6H), 3.75 (t, 2H, J=6.4 Hz), 4.61 (s, 2H), 4.84 (s, 2H), 6.76 (t, 1H, J=7.6 Hz), 6.84 (d, 2H, J=8 Hz), 7.12 ((t, 1H, J=7.6 Hz), 7.21-7.26 (m, 4H), 7.38-7.42 (m, 2H), 7.57 (t, 2H, J=6.4 Hz), 7.82 (dd, 1H, J=7.6 and 1.2 Hz); MS for C37H43FN4O4 m/z 627.4 (M+H)+.

Provenance & Evidence