Triacetoxyperiodinane → 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-furan-2-yl)-ethanone
Reaktionsgleichung
[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]([OH:26])[CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]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]=[CH:17][CH:18]=[C:13]3[CH:12]=[C:11]2[C:19](=[O:26])[CH2:20][CH:21]2[CH2:25][CH2:24][CH2:23][O:22]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
To a solution of 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-furan-2-yl)-ethanol (0.9 g, 2.4 mmol) in dichloromethane (100 mL) was added Dess-Martin periodinane (2.56 g, 6 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 dichloromethane (50 mL), washed with a saturated aqueous sodium bicarbonate solution (3×100 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 1-(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-2-(tetrahydro-furan-2-yl)-ethanone (0.5 g, 56%) as a light yellow solid: LC/MS m/e calcd for C19H18N2O4S [M+H]+ 371.43, observed 371.2.
Aufarbeitung
- customquenched with a saturated aqueous sodium bicarbonate solution (100 mL)
- extractionThe mixture was extracted with dichloromethane (50 mL)
- washwashed with a saturated aqueous sodium bicarbonate solution (3×100 mL), brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-7f24a0030a69423c8fdc091e11a6ac3d
- Quelldatensatz
- uspto-grants-2012_07
- Patentnummer
- US08222416B2
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