Potassium Carbonate → Methyl 6-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-pyridinecarboxylate

HRID 1690121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1690121
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[F:32]>CC(C)=O>[F:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 67968alpha-Bromo-o-fluorotolueneHCID 136146660Methyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate

Produkt 1

HCID 59468948Methyl 6-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-2-pyridinecarboxylateAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of methyl 6-(4-hydroxyphenyl)-2-pyridinecarboxylate (D80, 650 mg, 2.84 mmol) in acetone (8 ml) were added K2CO3 (780 mg, 5.67 mmol) and 1-(bromomethyl)-2-fluorobenzene (805 mg, 4.26 mmol). The mixture was stirred at 60° C. under nitrogen atmosphere for 6 h. Solvent was removed under reduced pressure and the residue was dissolved in AcOEt. The organic phase was washed with water, dried over Na2SO4, filtered and evaporated to dryness. The crude compound was purified by flash chromatography on 25 g silica gel cartridge, using a gradient of cyclohexane/ethylacetate 10/0 to 8/2 as eluent, to give the title compound (700 mg, 73%).

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in AcOEt
  3. washThe organic phase was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude compound was purified by flash chromatography on 25 g silica gel cartridge

Quellen und Nachweise

ORD-Eintrag
ord-30b2978232104efcbb5a853b8c43ac13
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153623B2

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