Cesium carbonate → 4-Chloro-9H-dipyrido[2,3-b;4',3'-d]pyrrole

Participants

Reaction Steps

A mixture of 4-chloro-9-(2-trimethylsilanyl-ethoxymethyl)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (1 eq.), the appropriate amine (5 eq.), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.2 eq), tris(dibenzylideneacetone)dipalladium(0) (0.1 eq.), and cesium carbonate (2 eq.) in 1,4-dioxane was heated between 100° C. to 110° C. until the reaction deemed complete. The reaction mixture was cooled then diluted with water and extracted with an appropriate solvent. The resultant residue was purified by flash chromatography on silica using either an ethyl acetate in heptane or methanol in dichoromethane gradient. The purified material was then deprotected using the conditions described below.

Provenance & Evidence