3-Aminopyridine → 4-chloro-N-pyridin-3-ylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

pyridin-3-amine (95 mg, 1.01 mmol), 2,4-dichloropyridine (0.151 mL, 1.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (70.4 mg, 0.12 mmol) and cesium carbonate (660 mg, 2.03 mmol) were stirred in dioxane (5 mL). The mixture was purged with nitrogen for 10 minutes. Palladium(II) acetate (22.76 mg, 0.10 mmol) was added and the mixture heated at 100 °C for 2h. The mixture was cooled, filtered and concentrated. The crude product was purified by flash silica chromatography, eluting gradient 5-45% EtOAc in isohexane. Fractions were evaporated to dryness and purified by flash silica chromatography, eluting at 35% EtOAc in isohexane to afford 4-chloro-N-(pyridin-3-yl)pyridin-2-amine (107 mg, 51.5 %) as a cream powder.

Provenance & Evidence