Selectfluor → 4-Fluoro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole

5-(2-Methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole (300.0 mg, 1.29 mmol) was dissolved in ACN (15 ml) in a polypropylene 20 mL scintillation vial. To this solution, Selectfluor (913.9 mg, 2.58 mmol) was added and the mixture was degassed with argon and heated to 80° C. for 6 hours. The solvent was removed under reduced pressure and the residue was dissolved in 50 mL EtOAc and 30 mL 3N HCl. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×50 ml). The organic layers were combined, dried over Na2SO4, filtered, and the solvent removed under reduced pressure. The residue was then purified by flash chromatography (Biotage SiO2, Hexanes (0.01% TEA)/EtOAc gradient elution) to afford 108 mg (33%) of 4-fluoro-5-(2-methoxy-5-nitro-phenyl)-1-methyl-1H-pyrazole as a white solid. LCMS m/z (%)=252 (M+H, 100). 1H NMR (400 MHz, CDCl3) δ: 8.39 (d, J=9.2 Hz, 1H), 8.22 (s, 1H), 7.44 (d, JH,F=4.4 Hz, 1H), 7.12 (d, J=9.2 Hz, 1H) 3.98 (s, 3H), 3.77 (s, 3H). 19F NMR (376 MHz, CDCl3) δ: −175.50 (d, JH,F=5.3 Hz, 1F).

1. customthe mixture was degassed with argon
2. customThe solvent was removed under reduced pressure
3. dissolutionthe residue was dissolved in 50 mL EtOAc
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with EtOAc (2×50 ml)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customthe solvent removed under reduced pressure
9. customThe residue was then purified by flash chromatography (Biotage SiO2, Hexanes (0.01% TEA)/EtOAc gradient elution)

ORD 기록

ord-010edfb0e80c44998c7e00215cbdb916

출처 데이터셋

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08871797B2