A mixture of 5-amino-2-chlorobenzonitrile (1.3 g, 8.58 mmol), tris(dibenzylideneacetone)dipalladium (0.192 g, 0.209 mmol), N-methyl-5-cyanopyrroleboronic acid (2.55 g, 17.16 mmol), and potassium fluoride (1.81 g, 31.25 mmol) in tetrahydrofuran (20 mL) was stirred under nitrogen. Tri-tert-butylphosphine (10% solution in hexane, 1.23 mL, 0.414 mmol) was added to the mixture and allowed to stir 3 hours at 50° C. until the starting bromide was consumed. The mixture was then diluted with 1/1 hexane/tetrahydrofuran and filtered through a plug of silica gel. The solvent was evaporated and the residue was purified by silica gel column chromatography (hexane/ethylacetate, 90/10 to 50/50) to afford the title compound (1.77 g, 92%).
