Ammonium Chloride → (5-Fluoro-2-nitrophenyl)-(5-fluoropyridin-3-yl)amine

Participants

Reaction Conditions

Reaction Steps

LiHMDS (1.0M in THF, 10.0 mL, 10.0 mmol) was added dropwise to a stirred solution of 3-amino-5-fluoropyridine (588 mg, 5.26 mmol) in anhydrous THF (10 mL) under a nitrogen atmosphere at −78° C. After 20 min 2,4-difluoro-1-nitrobenzene (0.55 mL, 5.0 mmol) was added and stirring at −78° C. was continued for 1 h. The reaction mixture was poured into a saturated aqueous solution of NH4Cl (50 mL). The aqueous phase was extracted with EtOAc (×2) and the combined organic fractions washed with brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% EtOAc in DCM) to afford the title compound as an orange solid (428 mg, 34%). LCMS (Method C): RT 3.27 min [M+H]+ 252.16

Provenance & Evidence