Synthesis of Indolo[2,3-d]benzazepinone Derivatives

2-Iodobenzonitrile, ethyl-1H-indole-carboxylate and 5-bromo-ethyl-1H-indole-carboxylate were purchased from ABCR. Borane solution (1M in THF), absolute DMF, dimethylaminopyridine, di-tert-butyl-dicarbonate, absolute acetonitrile, palladium(II) acetate, sodium bicarbonate, basic aluminuim oxide, 2-acetylpyridine and 2-formylpyridine were bought from Fisher/Acros Organics. Ethoxy-methylchloride was obtained form TCI. Sodium hydride, phosphorus(V) sulfide, celite, hydrazine monohydrate and methyl iodide were purchased from Sigma Aldrich, while lithium hydroxide monohydrate and triphenylphosphine were from Alfa Aesar. 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide-hydrochloride was purchased from IRIS biotech. Silver(I) carbonate was purchased from Merck. 2-Iodobenzylamine was prepared by a known method.^{26 (link)} The unsubstituted indolo[2,3-d]benzazepinone (A) was prepared by following published protocols.^{18 (link)–20} The 11-bromo-substituted B was prepared using reported precedures,^{18 (link)–20} with some modifications, a detailed description of the synthesis of B is given in the Supplementary Information file.