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Novel palladium-catalyzed cascade reaction of 2-methylindoles with 2- iodobenzyl bromide in the system Pd(OAc)2 / Xantphos / t-BuOK / toluene leading to indole- fused tricyclo[7,3,1,02,7] trideca-2(7),3,5-triene ring system was presented. Palladium catalyzed reaction of 2-methylindoles with 6-bromo-5-bromomethylbenzo[1,3] dioxole leads to 3,3-bis(6-bromobenzo[1,3]dioxol-5-ylmethyl)-2-methyl-3H-indoles.