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

HRID 1843622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1843622
[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-301542724e3b4fe18a94e62a3f2811c2
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946250B2

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