Cesium carbonate → 4-[3-(3-bromophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridine

HRID 45834Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 45834
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:25][O:26][C:27]1[CH:34]=[CH:33][C:30]([CH2:31]Cl)=[CH:29][CH:28]=1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:11][N:10]([CH2:31][C:30]3[CH:33]=[CH:34][C:27]([O:26][CH3:25])=[CH:28][CH:29]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 699934-Methyloxybenzyl chlorideHCID 178419384HCID 178419384, Verbindung

Produkt 1

HCID 671844264-[3-(3-bromophenyl)-1-(4-methoxybenzyl)-1H-pyrazol-4-yl]pyridineAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3 g (0.01 mol) of 4-[3-(3-bromophenyl)-1H-pyrazol-4-yl]pyridine were dissolved in 50 ml of dry dimethylformamide and 3.9 g (0.012 mol) of cesium carbonate and 1.6 ml (0.012 mol) of p-methoxybenzyl chloride were added. The mixture was stirred at 70° C. for 2 hours and the solvent removed in vacuo. The residue was taken up with dichoromethane and washed with water. The organic phase was dried over Na2SO4 and evaporated. Purification by column chromatography (dichloromethane-acetone 95/5) afforded 2 g (48% yield) of the title compound as an oil.

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated
  5. customPurification by column chromatography (dichloromethane-acetone 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-a8fe0974bf014553a118fc885054c8f3
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541575B2

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