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

HRID 1515780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515780
[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])=[C:23]([C:29]([F:32])([F:31])[F:30])[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:26]=[CH:25][C:24]([S:27][CH3:28])=[C:23]([C:29]([F:30])([F:32])[F:31])[CH:22]=2)=[O:20])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

4

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 67229160(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanol

Produkt 1

HCID 67229462(1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanoneAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a 250 mL round bottomed flask charged with (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanol (4.78 g, 10 mmol) and dichloromethane (50 mL) was added Dess-Martin periodinane (10.65 g, 25 mmol) at 25° C. The reaction mixture was stirred at 25° C. for 2 h before quenching with saturated aqueous sodium bicarbonate solution (100 mL). The mixture was extracted with ethyl acetate (250 mL), washed with saturated aqueous sodium bicarbonate solution (3×50 mL), brine, dried over anhydrous sodium sulfate and then concentrated in vacuo to give (1-benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-(4-methylsulfanyl-3-trifluoromethyl-phenyl)-methanone as a light yellow solid (3.8 g, 80%) which was used for the next step without further purification: LC/MS m/e calcd for C22H16F3N2O3S2 [M+H]+ 477.05, observed 477.0.

Aufarbeitung

  1. custombefore quenching with saturated aqueous sodium bicarbonate solution (100 mL)
  2. extractionThe mixture was extracted with ethyl acetate (250 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (3×50 mL), brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d834d4683f874de5a780c813bce6428f
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222416B2

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