The required, air-sensitive 6-or 7-indolols 4b were prepared ex tempore from commercially available benzyloxyindoles 4a though hydrogenolytic debenzylation. Apparently straightforward carbamoylation with carbamoyl chlorides 4c (route A, Scheme 4) in the presence of different bases led to a mixture of products. Presumably C3-alkylation is facile, as well, due to the electron-rich character of these indolols. Therefore, a cleaner alternative was soughtroute B via N,N-dialkylcarbamoylimidazolium salts 4e in the presence of N,Ndiisopropylethylamine (DIPEA) provided only the desired O-carbamoylated product 4f. This route offers additional advantages; for instance, the greater commercial availability of disubstituted amines vs. carbamoyl chlorides, it avoids the use of highly toxic (di-, tri-)phosgene, and is also exceptionally mild and therefore suitable for sensitive or polyfunctional amines (e.g., as in 21, 22). The final compounds were then facilely prepared in one additional step -Mannich reaction of indole carbamates 4f with formaldehyde and 2-cycloheptyl-Nmethylethan-1-amine in acetic acid at room temperature. This last reaction step was carefully chosen to allow for gentle reaction and isolation conditionsnamely, the absence of strong acids or bases, which could destroy labile electrophilic warheads.