Forty-five sulfonylated 7-azaindol-1-yl-acetonitriles have been prepared by a silver triflate mediated reaction assisted by microwave irradiation. Moderate to good yields were obtained in the first attempt in most cases. Poor yields were rapidly optimized using microwave. Alternative catalyst/solvent conditions were explored using microwave. We also report the microwave acceleration of a copper catalyzed 5-Chloro-7-azaindole cyclization. Together these microwave-assisted procedures provided a quick route to inverted 7-azatryptamine 3-aryl-sulfone arrays upon reduction of the acetonitrile protection group.