2-Aminopyridine → (5-Fluoro-2-nitrophenyl)pyridin-2-yl-amine

Participants

Reaction Conditions

Reaction Steps

LiHMDS (1.0M in THF, 4.8 mL, 4.8 mmol) was added dropwise to a stirred solution of pyridin-2-ylamine (269 mg, 2.86 mmol) in anhydrous THF (10 mL) under a nitrogen atmosphere at −78° C. After 30 min stirring at −78° C., 2,4-difluoro-1-nitrobenzene (298 μL, 2.72 mmol) was added and stirring at −78° C. was continued for 30 min. The reaction mixture was slowly warmed to RT and after 30 min quenched by addition of an aqueous solution of NH4Cl (50 mL). The mixture was partitioned between EtOAc and water, then filtered through Celite®. The organic fraction was dried (Na2SO4), concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane) to afford the title compound as an orange solid (258 mg, 41%). 1H NMR (CDCl3, 400 MHz): δ 10.48 (1H, s), 8.82 (1H, dd, J=12.32, 2.77 Hz), 8.38 (1H, dd, J=5.03, 1.87 Hz), 8.34-8.25 (1H, m), 7.70-7.64 (1H, m), 7.03-6.94 (2H, m), 6.68-6.61 (1H, m).

Provenance & Evidence