Cesium carbonate → 2-{[5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-yl]oxy}ethyl Acetate

HRID 1368662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1368662
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([OH:14])[C:3]=1[C:15]1[CH:23]=[CH:22][C:18]2[O:19][CH2:20][O:21][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:30]([O:33][CH2:34][CH2:35]Br)(=[O:32])[CH3:31]>CN(C)C=O>[C:30]([O:33][CH2:34][CH2:35][O:14][C:4]1[C:3]([C:15]2[CH:23]=[CH:22][C:18]3[O:19][CH2:20][O:21][C:17]=3[CH:16]=2)=[C:2]([NH2:1])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=1)(=[O:32])[CH3:31]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178507199HCID 178507199, Verbindung

Produkt 1

HCID 222819442-{[5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-yl]oxy}ethyl AcetateAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred mixture of 5-amino-4-(1,3-benzodioxol-5-yl)-1-benzyl-1H-pyrazol-3-ol (30 g) (Preparation 59) and cesium carbonate (94.8 g) in anhydrous dimethylformamide (340 ml), under an atmosphere of nitrogen, 2-bromoethyl acetate (16.2 g) was added drop-wise over 10 minutes and the reaction was stirred overnight. The reaction was quenched by the addition of an aqueous solution of HCl (2N, 260 ml) then ethyl acetate (600 ml) and water (100 ml) were added. The aqueous phase was extracted with ethyl acetate (3×500 ml) and the combined organic fractions were washed with brine (500 ml) and dried over Na2SO4. The dark oil was purified by flash chromatography (heptane/EtOAc; 1/1) (silica, 1000 g) yielding of the title compound as a dark oil (22.5 g).

Aufarbeitung

  1. customThe reaction was quenched by the addition of an aqueous solution of HCl (2N, 260 ml)
  2. additionethyl acetate (600 ml) and water (100 ml) were added
  3. extractionThe aqueous phase was extracted with ethyl acetate (3×500 ml)
  4. washthe combined organic fractions were washed with brine (500 ml)
  5. dry with materialdried over Na2SO4
  6. customThe dark oil was purified by flash chromatography (heptane/EtOAc; 1/1) (silica, 1000 g)

Quellen und Nachweise

ORD-Eintrag
ord-31c839139be3409794c99a0250a954a2
Quelldatensatz
uspto-grants-2003_06
Patentnummer
US06573270B1

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