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The generation of 4-, 5-, and 6-methoxy-3-indolylzinc chlorides 3a-c and their Pd(0)-catalyzed cross-coupling reactions with 2-halopyridines to give 4-, 5-, and 6-methoxy substituted 2-(2- pyridyl)indoles 4a-c is reported. 2-(2-Pyridyl)indole 8 is converted to indolo(2,3-a)quinolizidine 15. The key step is the regioselective cyclization on the indole 3-position of a thionium ion generated by Pummerer reaction from an appropriately substituted 2-(2-piperidyl)indole.

Pd(0)-catalyzed cross-coupling reactions of 2-indolylzinc halides. A convenient route to indolo[2,3-a]quinolizidines