Potassium Carbonate → (5-Chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methanone

HRID 2091261Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2091261
[Cl:1][C:2]1[N:7]=[C:6]([C:8](=O)[CH3:9])[C:5]([OH:11])=[CH:4][CH:3]=1.Br[CH2:13][C:14]([CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)=[O:15].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:9])=[C:13]([C:14]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[O:11][C:5]2=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 111600272-Bromo-1-cyclohexylethanoneHCID 722139671-(6-Chloro-3-hydroxypyridin-2-YL)ethan-1-one

Produkt 1

HCID 86662745(5-Chloro-3-methylfuro[3,2-b]pyridin-2-yl)(cyclohexyl)methanoneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 1-(6-chloro-3-hydroxypyridin-2-yl)ethanone (4.89 g) synthesized above, 2-bromo-1-cyclohexylethanone (7.01 g) synthesized in Example A51(1) and N,N-dimethylformamide (50 mL) was added potassium carbonate (11.8 g), and the mixture was stirred overnight at room temperature. Saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (5.78 g, 73%) as a white solid.

Aufarbeitung

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-33875e527edc446e83e6db5fa55aabbb
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436043B2

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