Ammonium Chloride → HCID 68157606, compound

Participants

Reaction Conditions

Reaction Steps

LiHMDS (1.0M in THF, 4.0 mL, 4.0 mmol) was added dropwise to a stirred solution of 5-fluoropyridin-2-ylamine (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 30 min. The mixture was slowly warmed to 0° C. then the reaction mixture poured into a saturated solution of NH4Cl (50 mL). The aqueous phase was extracted with EtOAc (×3) and the combined organic fractions washed with water, followed by brine, dried (Na2SO4) and concentrated in vacuo. 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 (34 mg, 7%). LCMS (Method C): RT 3.81 min [M+H]+ 252.1.

Provenance & Evidence