Ammonium Chloride → HCID 68157606, compound

Temperature

-78 °C

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.

1. stirringstirring at −78° C.
2. waitwas continued for 30 min
3. temperatureThe mixture was slowly warmed to 0° C.
4. extractionThe aqueous phase was extracted with EtOAc (×3)
5. washthe combined organic fractions washed with water
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-40% EtOAc in cyclohexane)

ORD record

ord-b92db4a153ea4817af59bfef76e47a58

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08653089B2