Aniline → 6-chloro-N-phenylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

2,6-dichloropyridine (228 mg, 1.54 mmol) was dissolved in toluene (7.5 ml) and diacetoxypalladium (6 mg, 0.03 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthalene (19 mg, 0.03 mmol), aniline (0.170 ml, 1.87 mmol) and potassium carbonate (583 mg, 4.22 mmol) were added added. The reaction mixture was sparged with notrogen for 3-4 minutes before being sealed into a microwave tube and heated to 160 °C over ~3 minutes, before holding at that temperature for 30 minutes. After cooling to ambient temperature the reaction mixture was diluted to ~40 mL with ethyl acetate and insoluble material removed by filtration. The filtrate was evaporated and purification attempted by flash silica chromatography, elution gradient 0 to 50% EtOAc in heptane. Product containing fractions were evaporated to dryness to afford 6-chloro-N-phenylpyridin-2-amine (167 mg, 53.0 %) as a waxy pale yellow solid

Provenance & Evidence