Synthesis of Indolo-Benzazepin Derivatives

2-Iodobenzonitrile,
indole-3-carboxaldehyde, and 5-bromoindole-3-carboxaldehyde
were purchased from ABCR. Borane solution (1 M in THF), absolute DMF,
4-dimethylaminopyridine (DMAP), di-tert-butyl-dicarbonate
(Boc₂O), absolute acetonitrile (ACN), palladium(II) acetate,
sodium bicarbonate, tetrabutylammoinium fluoride (TBAF), basic aluminium
oxide, and 2-formylpyridine were bought from Fisher/Acros Organics.
2-Acetylpyridine was obtained from TCI. Sodium hydride (NaH, 60% dispersion
in mineral oil), copper(II) chloride dihydrate, p-toluenesulfonyl chloride, phosphorus pentasulfide, methanol, DCM,
THF, ethyl acetate (EtOAc), hexane, celite, and hydrazine monohydrate
were purchased from Sigma-Aldrich. EDCI·HCl was obtained from
IRIS biotech, while silver(I) carbonate was purchased from Merck.
2-Iodobenzylamine was prepared by a known method.^{65 (link)} The proligands HL⁵–HL¹¹ and the corresponding
complexes 5–11 were prepared as reported previously,^{33 (link),39 (link)} while 5,12-dihydroindolo[3,2-d]benzazepin-7(6H)-one was synthesized by following a literature protocol.^{37 (link)} Absolute hydrazine was preabsoluted over sodium
hydroxide.