Triacetoxyperiodinane → (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanone

HRID 1515881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515881
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[CH:19]([C:21]2[CH:26]=[CH:25][C:24]([S:27][CH3:28])=[CH:23][CH:22]=2)[OH:20])(=[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]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19]([C:21]2[CH:22]=[CH:23][C:24]([S:27][CH3:28])=[CH:25][CH:26]=2)=[O:20])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 67229059(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanol

Produkt 1

HCID 67227743(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanoneAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanol (7.0 g, 17.1 mmol) in dichloromethane (600 ml) was added Dess-Martin periodinane (21.8 g, 51.3 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 (100 mL). The mixture was extracted with ethyl acetate (500 mL), washed with a saturated aqueous sodium bicarbonate solution (3×80 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo. Purification by flash column chromatography (silica gel from QingDao, 200-300 mesh, 30% ethyl acetate/hexanes) afforded (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-phenyl)-methanone (6.73 g, 97%) as a white solid: LC/MS m/e calcd for C21H16N2O3S2 [M+H]+ 409.50, observed 409.2.

Aufarbeitung

  1. customquenched with a saturated aqueous sodium bicarbonate solution (100 mL)
  2. extractionThe mixture was extracted with ethyl acetate (500 mL)
  3. washwashed with a saturated aqueous sodium bicarbonate solution (3×80 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash column chromatography (silica gel from QingDao, 200-300 mesh, 30% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fa1c8fa5d3394bb0be8073a2a26ca40a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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