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

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Reaction Conditions

Reaction Steps

LiHMDS (1.0M in THF, 4.0 mL, 4.0 mmol) was added dropwise to a stirred solution of 2-amino-3-fluoropyridine (224 mg, 2.0 mmol) in anhydrous THF (5 mL) under a nitrogen atmosphere at −78° C. After 15 min stirring at −78° C., a solution of 2,4-difluoro-1-nitrobenzene (0.22 mL, 2.0 mmol) in THF (5 mL) was added and stirring at −78° C. was continued for 1 h. The mixture was slowly warmed to 0° C. and stirring continued for 1 h. The crude solution was poured into a saturated aqueous solution of NH4Cl (50 mL). The aqueous phase was extracted with EtOAc (×3) and the combined organic fractions were washed with water, followed by brine, dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-100% DCM in cyclohexane) to afford the title compound as an orange solid (93 mg, 19%). LCMS (Method C): RT 3.97 min [M+H]+ 252.10.

Provenance & Evidence