Potassium Carbonate → HCID 67333397, Verbindung

HRID 1804820Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1804820
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.Br[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:24][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[CH:3]=[CH:2]2)=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 22645461Methyl 5-(bromomethyl)-2-fluorobenzoateHCID 178516385quinolin-4-ol

Produkt 1

HCID 67333397HCID 67333397, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of quinolin-4-ol, methyl 5-(bromomethyl)-2-fluorobenzoate (prepared as described in US 2007/0021427 A1, 1 eq) and potassium carbonate (1.2 eq) in dry DMF (0.1 M solution) was stirred at 100° C. for 1 h. After solvent evaporation, the residue was dissolved in DCM and washed twice with H2O and once with brine. The organic phase was dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting crude was purified by flash-chromatography (EtOAc/PE 9:1) to give the title compound. The O-alkylated isomer is eluted before the title compound.

Aufarbeitung

  1. customAfter solvent evaporation
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed twice with H2O and once with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resulting crude was purified by flash-chromatography (EtOAc/PE 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-82638a5427384b5290c151f5c9ff24a0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354413B2

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