Sodium Iodide → tert-butyl 1-(3-(3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)propyl)-1H-indole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of benzyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (807 mg, 1.65 mmol, 1 equiv), tert-butyl 1-(3-chloropropyl)-1H-indole-2-carboxylate (507 mg, 1.65 mmol, 1 equiv), sodium iodide (123.3 mg, 0.823 mmol, 0.5 equiv) and potassium carbonate (684.1 mg, 4.95 mmol, 3 equiv) in 2-butanone was stirred at 81° C. for 16 h. After cooling the reaction mixture, the crude mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, concentrated, and the crude residue was purified using the Biotage flash chromatography system (SNAP 50 g cartridge, Rf=0.2, gradient—10%-50% ethyl acetate in hexanes) to afford the title compound as an oil (230 mg, 19%); MS for C44H48N4O5 m/z 713.37 (M+H)+.

Provenance & Evidence