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

Participants

Reaction Steps

tert-Butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate) (0.25 g, 0.593 mmol), 1′-(3-chloropropyl)spiro[cyclopropane-1,3′-indolin]-2′-one) (0.14 g, 0.593 mol), sodium iodide (0.027 g, 0.178 mmol), and potassium carbonate (0.12 g, 0.890 mmol) in 2-butanone (8 mL) were heated at 78° C. for 4 hours. The reaction was diluted with 10% methanol/dichloromethane, filtered, and evaporated. The residue was purified by PTLC (5% methanol/dichloromethane) to give product as a white solid (0.27 g, 72%); 1H NMR (DMSO-d6); δ1.51 (s, 9H); 1.53-1.63 (m, 6H); 1.80 (m, 2H); 2.37 (m, 2H); 2.51-2.63 (m, 2H); 2.63-2.76 (m, 4H); 3.82 (t, J=6.8 Hz, 2H); 4.58 (s, 2H); 4.61 (s, 2H); 6.76 (t, J=7.2 Hz, 1H); 6.85 (d, J=8.4 Hz, 2H); 6.98-7.00 (m, 2H); 7.19-7.24 (m, 4H); 7.49-7.56 (m, 2H); 7.79 (s, 1H); 7.82-7.84 9M, 1H); MS for C38H44N4O4 m/z 621 (M+H)+.

Provenance & Evidence