A straightforward synthesis of 1,3-dichloro-5,8-dihydroisoquinoline by consecutive Stille cross-coupling and metathesis reactions

An efficient three-step synthetic route from 2,6-dichloro-4-iodopyridine to 1,3-dichloro-5,8-dihydroisoquinoline is described. A ring-closing-metathesis reaction constitutes the key step in this synthetic sequence. The reactivity of both chloro atoms is demonstrated in a Suzuki arylation reaction. (C) 2009 Elsevier Ltd. All rights reserved.