Sodium hydride → tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate

HRID 512862Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512862
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH:24]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1)(C1C=CC(C)=CC=1)(=O)=O>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[CH:24]2[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 157347131-(tert-Butoxycarbonyl)-4-(p-toluenesulfonyloxy)piperidineHCID 178423506-Fluoro-1H-indazole

Produkt 1

HCID 89614504tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 6-fluoro-1H-indazole (6.46 mmol, 880 mg) in DMF (15 mL) cooled to 0° C. under Ar was added 95% NaH (6.46 mmol, 163 mg). The resulting mixture was stirred for 15 minutes before tert-butyl 4-(tosyloxy)piperidine-1-carboxylate (7.11 mmol, 2.52 g) was added. After an additional 15 minutes at 0° C., the ice bath was removed and the reaction vessel placed in a 110° C. bath for 2.75 hours. After cooling to ambient temperature, the DMF was removed in vacuo and ethyl acetate (100 mL) was added. The organic layer was washed with water and brine, dried (MgSO4), filtered and the solvent removed in vacuo. The resulting residue was purified by SiO2 column chromatography (0-40% EtOAc/hexanes) to yield tert-butyl 4-(6-fluoro-1H-indazol-1-yl)piperidine-1-carboxylate.

Aufarbeitung

  1. additionwas added
  2. customthe ice bath was removed
  3. customplaced in a 110° C.
  4. customfor 2.75 hours
  5. customthe DMF was removed in vacuo and ethyl acetate (100 mL)
  6. additionwas added
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe solvent removed in vacuo
  11. customThe resulting residue was purified by SiO2 column chromatography (0-40% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ddaf614fcc5d4af485d6b4ee1e9fa421
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102669B2

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