Perfluoro-1-butanesulfonyl fluoride → HCID 58110138, Verbindung

Step AAH (7): To a soln of 7-phenyl-4,5-dihydropyrazolo[1,5-a]pyridin-2-ol (500 mg, 2.356 mmol) in THF (15 mL) was added NaHMDS (1.0 M in THF, 2.94 mL, 2.94 mmol) at −78° C. under nitrogen. After stirring for 10 min, 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonyl fluoride (1281 mg, 4.24 mmol) was added. The mixture was allowed to warm from −78° C. to rt over 3 h. The reaction was diluted with EtOAc (200 mL) and washed sequentially with 0.1 N aqueous sodium hydroxide, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (30% EtOAc/hexanes) to afford 7-phenyl-4,5-dihydropyrazolo[1,5-a]pyridin-2-yl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (1.0 g, 86% yield). LC-MS (M+H)+ 495.12.

1. temperatureto warm from −78° C. to rt over 3 h
2. washwashed sequentially with 0.1 N aqueous sodium hydroxide, water, and brine
3. dry with materialThe organic layer was dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customThe residue was purified

ORD-Eintrag

ord-b8b3a67e0ab34b18b4d9f92cee09bf42

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08349880B2