Methanol → 1-[6-(5-{1-[3-fluoro-4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1882008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882008
[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:18]2[NH:22][C:21]([C:23]3[N:28]=[CH:27][C:26]([CH:29]([OH:32])[CH2:30][OH:31])=[CH:25][CH:24]=3)=[CH:20][CH:19]=2)[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1SC.O1CCC[CH2:34]1.CO.O[O:41][S:42]([O-:44])=O.[K+]>C(OCC)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:18]2[NH:22][C:21]([C:23]3[N:28]=[CH:27][C:26]([CH:29]([OH:32])[CH2:30][OH:31])=[CH:25][CH:24]=3)=[CH:20][CH:19]=2)[CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[S:42]([CH3:34])(=[O:44])=[O:41]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593313981-[6-(5-{1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

Produkt 1

HCID 593315531-[6-(5-{1-[3-fluoro-4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diolAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1-[6-(5-{1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol (367 mg) in a mixed solvent of tetrahydrofuran (3 mL), methanol (3 mL) and water (3 mL) was added Oxone (registered trademark) (593 mg), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (330 mg, 84%) as a pale-yellow amorphous solid. MS: 489 (MH+).

Aufarbeitung

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-71305c37c1504839b000fd1a9cd01ddd
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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