Triacetoxyperiodinane → 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanone

HRID 1515895Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515895
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[CH:20]([OH:28])[CH2:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([F:19])[CH:18]=[C:13]3[CH:12]=[C:11]2[C:20](=[O:28])[CH2:21][CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 672276021-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanol

Produkt 1

HCID 672277401-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanoneAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanol (1.23 g, 3.04 mmol) in dichloromethane (100 ml) was added Dess-Martin periodinane (3.87 g, 9.12 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 1 h and then quenched with a saturated aqueous sodium bicarbonate solution (60 mL). The mixture was extracted with ethyl acetate (150 mL), washed with a saturated aqueous sodium bicarbonate solution (3×30 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 33% ethyl acetate/hexanes) to afford 1-(1-benzenesulfonyl-5-fluoro-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-pyran-4-yl)-ethanone (1.1 g, 90%) as a light yellow solid: LC/MS m/e calcd for C20H19FN2O4S [M+H]+ 403.45, observed 403.2.

Aufarbeitung

  1. customquenched with a saturated aqueous sodium bicarbonate solution (60 mL)
  2. extractionThe mixture was extracted with ethyl acetate (150 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×30 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel from QingDao, 200-300 mesh, 33% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-57c7260a347247528bfc445f5249a893
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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