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2 protocols using lithium hydroxide monohydrate

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

Purification of Hydroxide Electrolytes

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Lithium hydroxide monohydrate (99.995% metals basis) was purchased from Alfa Aesar. Sodium hydroxide (semiconductor grade, 99.99% trace metals basis) was purchased from Sigma-Aldrich. Potassium hydroxide (semiconductor grade, 99.99% trace metals basis) was purchased from Sigma-Aldrich. Rubidium hydroxide hydrate (15 to 20% H2O, 99% metals basis) was purchased from Alfa Aesar. Cesium hydroxide monohydrate (99.95% trace metals basis) was purchased from Sigma-Aldrich. The electrolytes used for all reactivity studies were purified with Chelex resin (Sigma-Aldrich, Chelex 100 sodium form). To further remove the trace metal contamination in 0.1 M RbOH, preelectrolysis of the electrolyte in an Ar atmosphere was carried out for 2 hours using electropolished Cu foil electrodes at a constant current density of −5 mA cm−2. The electrolyte pH, which was detected using the Orion Star A111 Benchtop pH Meter (Thermo Fisher Scientific), showed no significant change after the electrolysis.
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