Here,　we　report　an　unprecedented　gold(I)-induced　β-site　regioselective　formal　[3　+　2]　cycloaddition　of　ynamides　with　pyrido[1,2-b]indazoles,　giving　3-amido-7-(pyrid-2′-yl)indoles　in　good　to　excellent　yields.　A　complex　of　gold(I)　catalyst　with　ynamide　was　isolated　and　characterized　by　X-ray　diffraction　analysis　for　the　first　time.　Mechanistic　investigations　suggest　the　reaction　pathway　involves　a　gold-stabilized　carbocation　intermediate,　which　in　turn　participated　in　sequential　C-H　bond　functionalization　of　the　ortho-position　of　the　phenyl　ring.　©　2016　American　Chemical　Society.