Water → 2-(5-{1-[3-fluoro-4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridine

HRID 1882086Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882086
[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:18]2[NH:22][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N: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[CH2:30]1.O.O[O:36][S:37]([O-:39])=O.[K+]>C(OCC)(=O)C.CO>[F:1][C:2]1[CH:3]=[C:4]([CH:10]([C:18]2[NH:22][C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N: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:37]([CH3:30])(=[O:39])=[O:36]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593315702-(5-[1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine

Produkt 1

HCID 593314642-(5-{1-[3-fluoro-4-(methylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2-(5-[1-[3-fluoro-4-(methylsulfanyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl]-1H-pyrrol-2-yl)pyridine (97.8 mg), tetrahydrofuran (2 mL), water (2 mL) and methanol (2 mL) was added Oxone (registered trademark) (159 mg), and the mixture was stirred at room temperature for 4 hr. The reaction mixture was diluted with ethyl acetate, and washed with saturated aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (41.2 mg, yield 41%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (9:1, volume ratio). MS: 429 (MH+).

Aufarbeitung

  1. washwashed with saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe ethyl acetate layer was dried (MgSO4)
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec1b32c58d8d42cc8144632f8230f57d
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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