Methyl iodide → 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one

HRID 625951

Reaktionsgleichung

Reaktionsgleichung von HRID 625951
[CH2:1]([O:8][C:9]1[C:10]([OH:16])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[N:11]([CH3:17])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178517596HCID 178517596, Verbindung

Produkt 1

HCID 674178603-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-oneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(benzyloxy)-5-bromopyridin-2-ol ((5.8 g, 20.7 mmol) in DMF (75 mL) was added Cs2CO3 (8.8 g, 26.9 mmol). A solution of MeI (1.62 mL, 25.9 mmol) in DMF (10 mL) was added dropwise to this mixture. After stirring at room temperature for 3 h, the reaction mixture was concentrated. The residue was taken up in H2O and the aqueous solution was extracted with CH2Cl2 (3×). Combined organic solutions washed with brine (1×), dried over Na2SO4 and concentrated. Purification by flash chromatography (250 g silica gel, 50% EtOAc in hexanes) afforded 4.02 g (66%) of 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.43-7.32 (m, 5H), 7.05 (s, 1H), 6.91 (s, 1H), 5.11 (s, 2H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. extractionthe aqueous solution was extracted with CH2Cl2 (3×)
  3. washCombined organic solutions washed with brine (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by flash chromatography (250 g silica gel, 50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-4492883666e14f72a0e246ae91d6e31e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309199B2

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