Methyl iodide → 5-(2-Fluoropyridin-3-yl)-1-methylazepan-2-one

HRID 410253Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 410253
[F:1][C:2]1[C:7]([CH:8]2[CH2:14][CH2:13][NH:12][C:11](=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].I[CH3:19].[Cl-].[NH4+]>CN(C=O)C>[F:1][C:2]1[C:7]([CH:8]2[CH2:14][CH2:13][N:12]([CH3:19])[C:11](=[O:15])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 593268345-(2-Fluoropyridin-3-yl)azepan-2-one

Produkt 1

HCID 593270605-(2-Fluoropyridin-3-yl)-1-methylazepan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-fluoropyridin-3-yl)azepan-2-one (0.15 g, 0.72 mmol) in DMF (2.5 mL) under argon was added sodium hydride (0.021 g, 0.86 mmol). The mixture was stirred at room temperature for 15 min before iodomethane (0.054 mL, 0.86 mmol) was added via syringe. This mixture was stirred for 4 h at room temperature before saturated aqueous ammonium chloride was added. The mixture was extracted with ethyl acetate (2×) and the combined extracts were washed with water (3×), saturated aqueous sodium chloride (1×), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 5-(2-fluoropyridin-3-yl)-1-methylazepan-2-one. [M+1]=223.1.

Aufarbeitung

  1. additionwas added via syringe
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate (2×)
  4. washthe combined extracts were washed with water (3×), saturated aqueous sodium chloride (1×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dd3e310a5f9743c693bc784df44cc0ba
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759532B2

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