Sodium hydride → 4-((2-Bromopyridin-3-yl)methyl)morpholin-3-one

HRID 1517602Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517602
[Br:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][C:13]1=[O:18]>CN(C)C=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:7]([CH2:8][N:12]2[CH2:17][CH2:16][O:15][CH2:14][C:13]2=[O:18])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 669533-MorpholinoneHCID 109010782-Bromo-3-(bromomethyl)pyridine

Produkt 1

HCID 582686224-((2-Bromopyridin-3-yl)methyl)morpholin-3-oneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-bromo-3-bromomethyl-pyridine (0.68 g, 2.36 mmol) in dimethylformamide (10 mL) are added sodium hydride (0.11 g, 60% suspension, 2.82 mmol), morpholin-3-one (0.20 g, 1.97 mmol) and tetrabutylammonium iodide (catalytic) at 0° C. The mixture is stirred at room temperature for 16 hours. After completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL). The aqueous layer is extracted with ethyl acetate (2×25 mL) and the combined organic extracts are dried over sodium sulfate and concentrated in vacuo. The crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45) to yield 0.35 g (66%) of the title compound. MS (m/z): 271/273 (M+1, M+3).

Aufarbeitung

  1. customAfter completion, the reaction mixture is partitioned between ethyl acetate (25 mL) and water (25 mL)
  2. extractionThe aqueous layer is extracted with ethyl acetate (2×25 mL)
  3. dry with materialthe combined organic extracts are dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude material is purified by column chromatography over silica gel eluting with hexane/ethyl acetate (55:45)

Quellen und Nachweise

ORD-Eintrag
ord-eca5ef5598b44329a6130dbd66720b76
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232289B2

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