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2 protocols using silver 1 carbonate

1

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

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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.
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2

Synthesis of Indolo-Benzazepin Derivatives

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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 HL5HL11 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.
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