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

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 2-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.15 g, 0.34 mmol), sodium iodide (0.015 g, 0.1 mmol) and potassium carbonate (0.081 g, 0.51 mmol) in 2-butanone (4 mL), was added 1-(3-chloropropyl)-3,3-dimethylindolin-2-one (0.081 g, 0.34 mmol). After stirring at 78° C. for 18 hours, the reaction mixture was filtered and isolated by Biotage flash chromatography (1-10% methanol/dichloromethane) and preparatory TLC (10% methanol/dichloromethane) to obtain the title compound (0.18 g, 83%); 1H NMR (DMSO-d6): δ 1.25 (s, 6H), 1.56 (s, 9H), 1.67-1.75 (m, 4H), 2.31 (br, 4H), 2.64-2.66 (m, 4H), 3.72 (t, 2H, J=7.2 Hz), 4.58 (s, 2H), 4.82 (s, 2H), 6.90-6.91 (m, 2H), 7.02 (t, 1H, J=7.6 Hz), 7.08-7.12 (m, 3H), 7.19-7.27 (m, 2H), 7.33 (d, 1H, J=6.8 Hz), 7.40 (t, 1H, J=7.2 Hz), 7.57 (t, 1H, J=7.6 Hz), 7.82 (dd, 1H, J=7.2 and 1.2 Hz); MS for C38H45FN4O4 m/z 641.17 (M+H)+.

Provenance & Evidence