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The 4-iodo-β-carboline-3-carboxamide derivative 2 was obtained by orthodirected metalation of the phenylcarboxamide precursor 5 using methyllithium and iodine followed by in situ Nmethylation with methyl iodide. Compound 2 reacted with a variety of aryland heteroarylboronic acids under classical Suzuki–Miyaura palladium-catalyzed coupling conditions to give the corresponding 4-aryl (7a–d, 7f) and 4-heteroaryl (7g, 7h) β-carboline-3carboxamides. While this reaction failed in the case of 3,4,5-trimethoxyphenylboronic acid, conditions were found [Pd(OAc)2, dppf, CsF in dioxane–ethanol] which allowed formation of the coupled product 7e in high yield. The N,N-dimethylsulfamoyl protecting group was easily removed using a trifluoroacetic acid–trifluoromethanesulfonic acid mixture. Reductive amination of the 4-(2-formylphenyl)-β-carboline derivative 7f with benzylamine followed by sodium hydridepromoted cyclization provided the novel benzazepino-β-carboline derivative 9.

Preparation of 4-aryl-β-carboline-3-carboxamides by Suzuki–Miyaura cross-coupling applied to a 4-iodo precursor obtained by ortho- directed lithiation