A one-pot synthesis of the 2,3-dihydropyrrolo [3,2-c]quinolines

ORGN 729

Mirek Tomaszewski, Mirek.Tomaszewski@astrazeneca.com, Adam Whalley, Louis-David Cantin, Mirek.Tomaszewski@astrazeneca.com, and Yun-Jin Hu, Mirek.Tomaszewski@astrazeneca.com. Department of Chemistry, AstraZeneca R&D Montréal, 7171 Frédérick-Banting, St. Laurent (Montréal), QC H4S 1Z9, Canada
A one-pot synthesis of the 2,3-dihydropyrrolo[3,2-c]quinoline core from substituted 2-haloanilines was achieved using 10 mol% Pd(PPh3)4 in dioxane at 170 °C for 1 hour in a microwave oven. The reaction can be scaled up to a gram scale. The proposed mechanism involves a Heck reaction followed by intra-molecular Schiff base formation and double bond migration.