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

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 3-((1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (3 g, 6.81 mmol, 1 equiv), sodium iodide (0.408 g, 2.72 mmol, 0.4 equiv) and potassium carbonate (2.35 g, 13.62 mmol, 2 equiv) in 2-butanone (5 mL), was added 1′-(3-chloropropyl)spiro[cyclopropane-1,3′-indolin]-2′-one (1.61 g, 6.81 mmol, 1 equiv). After stirring at 78° C. for 16 hours, the reaction mixture was filtered and isolated using the Biotage flash chromatography system (SNAP 100 g cartridge, Rf=0.5, gradient—50%-100% ethyl acetate in hexanes) to obtain the title compound (2.84 g, 63%); 1H NMR (DMSO-d6): δ 1.52 (s, 9H), 1.57-1.65 (m, 6H), 1.77 (t, 2H, J=6.4 Hz), 2.25-2.37 (m, 4H), 2.64-2.68 (m, 4H), 3.79 (t, 2H, J=6.8 Hz), 4.57 (d, 4H, J=13.2 Hz), 6.91-7.20 (m, 8H), 7.48-7.51 (m, 2H), 7.78 (s, 1H), 7.83 (d, 1H, J=7.2 Hz); MS for C38H43FN4O4 m/z 639.14 (M+H)+.

Provenance & Evidence