5-bromo-4-fluoro-3,3-dimethyl-1,3-dihydro-2H-indol-2-one (1.25 g, 4.86 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.4 g) was dissolved in ethylene glycol dimethyl ether (40 mL) and stirred 15 minutes. N-methyl-5-cyanopyrroleboronic acid (2.0 g, 13.33 mmol) and potassium carbonate (3.48, 25 mmol) were added followed by water (20 mL) and the mixture heated under reflux (24 hours). The mixture was then poured into water, neutralized with dilute hydrochloric acid, and extracted with ethylacetate. The solvent was dried over magnesium sulfate, and concentrated in vacuo. Flash chromatography; SiO2, Hexane/THF 9/1 then 7/3 gave 5-(4-fluoro-3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrrole-2-carbonitrile (0.060 g, 5%):
