Water → 2-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfonyl)pyridine

HRID 1882123Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882123
[CH3:1][C:2]([C:21]1[CH:26]=[CH:25][C:24](SC)=[CH:23][N:22]=1)([C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[CH2:3][CH:4]1[CH2:9][CH2:8][O:7][CH2:6][CH2:5]1.O1CCC[CH2:30]1.O.O[O:36][S:37]([O-:39])=O.[K+]>C(OCC)(=O)C.CO>[CH3:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([S:37]([CH3:30])(=[O:39])=[O:36])=[CH:23][N:22]=1)([C:10]1[NH:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:13][CH:14]=1)[CH2:3][CH:4]1[CH2:5][CH2:6][O:7][CH2:8][CH2:9]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 23707502Potassium hydroxy sulfiteHCID 593312412-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine

Produkt 1

HCID 593315142-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfonyl)pyridineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of 2-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine (84.0 mg), tetrahydrofuran (1 mL), water (1 mL) and methanol (1 mL) was added Oxone (registered trademark) (157 mg), and the mixture was stirred at room temperature for 1.5 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 (55.5 mg, yield 61%) was obtained as white crystals from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). melting point 135-136° C. MS: 426 (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-1961fb1847f742b99b40b91e26933feb
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318746B2

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