摘要 |
<p>Disclosed are processes for the preparation of 2-substituted indole compounds wherein the 2-substituent comprises an R<SUB>4 </SUB>group, wherein R<SUB>4 </SUB>is selected from the group consisting of monocyclic aromatic, polycyclic aromatic, monocyclic heteroaromatic, polycyclic heteroaromatic, 1° alkyl, and alkenyl, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents, and wherein R<SUB>4 </SUB>is bonded to the 2-position of the indole ring via a C-C bond; the process comprising reacting an orthogem-dihalovinylaniline compound of the formula (I): wherein Halo comprises Br, Cl, or I; each of the one or more R<SUB>1 </SUB>is independently selected from the group consisting of H, fluoro, lower alkyl, lower alkenyl, lower alkoxy, aryloxy, lower haloalkyl, lower alkenyl, -C(O)O-lower alkyl, monocyclic or polycyclic aryl or heteroaryl moiety, or R<SUB>1 </SUB>is an alkenyl group bonded so to as to form a 4- to 20-membered fused monocycle or polycyclic ring with the indole ring; all of which are optionally substituted with one or more suitable substituents at one or more substitutable positions; R<SUB>2 </SUB>comprises H, alkyl, cycloalkyl, aryl, heteroaryl, aryl-loweralkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; R<SUB>3 </SUB>comprises H, alkyl, haloalkyl, alkenyl, alkynyl, aryl, heteroaryl, cycloalkyl, heterocycle, aryl-(C<SUB>1-6</SUB>)alkyl-, or heteroaryl-loweralkyl-, all of which are optionally substituted at one or more substitutable positions with one or more suitable substituents; with an organoboron reagent selected from the group consisting of a boronic ester of R<SUB>4</SUB>, a boronic acid of R<SUB>4</SUB>, a boronic acid anhydride of R<SUB>4</SUB>, a trialkylborane of R<SUB>4 </SUB>and a 9-BBN derivative of R<SUB>4</SUB>; in the presence of a base, a palladium metal pre-catalyst and a ligand under reaction conditions effective to form the 2-substituted indole compound. Also disclosed are processes for the preparation of ortho-gem-dihalovinylaniline compounds. Novel compounds prepared by the processes and novel uses of the compounds are likewise disclosed.</p> |