Synthesis of novel indole based cyclophanes and cylindrical cyclophanes by tandem alkylation methodology using NaH

Treatment of 1 equiv of 1,3-bis(bromomethyl)benzene and 2,6-bis(bromomethyl)pyridine with 1 equiv of indole in the presence of NaH in THF afforded the symmetrical cyclophanes 1 and 2. Using similar methodology, cylindrical cyclophanes 3 and 4 were obtained from 2 equiv of 1,3,5-trimethyl-2,4,6-tris(bromomethyl)benzene and 1,3,5-tris(bromomethyl)benzene with 3 equiv of indole.