Sodium Chloride → N-Cyclohexyl-5-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine

HRID 1506212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1506212
[CH:1]1([NH:7][C:8]2[C:9]3[CH:20]=[CH:19][NH:18][C:10]=3[N:11]=[CH:12][C:13]=2[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29].[Cl-].[Na+]>CN(C)C=O>[CH:1]1([NH:7][C:8]2[C:9]3[CH:20]=[CH:19][N:18]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:10]=3[N:11]=[CH:12][C:13]=2[S:14]([CH3:17])(=[O:16])=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 71258218N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine

Produkt 1

HCID 86726635N-Cyclohexyl-5-(methylsulfonyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amineAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-Cyclohexyl-5-(methylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-amine (7.0 mg, 0.024 mmol) in N,N-dimethylformamide (1 mL) was stirred with sodium hydride (55 wt % dispersion in mineral oil, 3.0 mg, 0.069 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (10 μL, 0.057 mmol) at room temperature for 2 hours. After addition of saturated aqueous sodium chloride, the reaction mixture was extracted with ethyl acetate, and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→3/1 (v/v)) to give the title compound as a colorless oil (6.1 mg, yield 60%).

Aufarbeitung

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→3/1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-5a14636c24624ae6816a42a143704c13
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216999B2

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