Cesium carbonate → 2-(Cyclopropylmethoxy)-5-iodopyridine

HRID 1888754Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1888754
[I:1][C:2]1[CH:3]=[CH:4][C:5]([OH:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH:17]1[CH2:19][CH2:18]1>CN(C=O)C.C(OCC)(=O)C>[CH:17]1([CH2:16][O:8][C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]=2)[CH2:19][CH2:18]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 81503BromomethylcyclopropaneHCID 4595002-Hydroxy-5-iodopyridine

Produkt 1

HCID 425531642-(Cyclopropylmethoxy)-5-iodopyridineAusbeute 32,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 5-iodopyridin-2-ol (5.32 g, 24.0 mmol) in DMF (50 mL) were added cesium carbonate (23.4 g, 72.0 mmol) and (bromomethyl)cyclopropane (4.67 mL, 48.2 mmol), and the mixture was stirred at 60° C. for 15 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed three times with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:4) to give the title compound (2.17 g, yield 32%) as an oil.

Aufarbeitung

  1. washthe mixture was washed three times with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-c8e0599cd84546b7816484fbb1f630f0
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501804B2

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