Water → HCID 23400310, Verbindung

HRID 397278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 397278
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([OH:8])[C:3]=1[C:9]1[CH:17]=[CH:16][C:12]2[O:13][CH2:14][O:15][C:11]=2[CH:10]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][CH2:26][O:27][C:28](=[O:30])[CH3:29].O>CN(C)C=O>[C:28]([O:27][CH2:26][CH2:25][O:8][C:4]1[C:3]([C:9]2[CH:17]=[CH:16][C:12]3[O:13][CH2:14][O:15][C:11]=3[CH:10]=2)=[C:2]([NH2:1])[N:6]([CH3:7])[N:5]=1)(=[O:30])[CH3:29]

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 135641-Acetoxy-2-bromoethaneHCID 178481945HCID 178481945, Verbindung

Produkt 1

HCID 23400310HCID 23400310, VerbindungAusbeute 35,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-amino-4-(1,3-benzodioxol-5-yl)-1-methyl-1H-pyrazol-3-ol (Preparation 16) (11.39 g) was dissolved in dimethylformamide (40 mm), caesium carbonate (15.9 g) was added followed by 2-bromoethylacetate (8.16 g). The mixture was stirred at room temperature for 16 hours. The mixture was treated with water (750 ml) and extracted with ethyl acetate (2×250 ml). The organic fractions were combined washed with water (3×350 ml), brine (250 ml), dried over magnesium sulfate, filtered and evaporated. The crude product was purified on. silica (300 g) eluting with ethyl acetate:hexane (3:1) to yield the title compound as a white solid (5.57 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×250 ml)
  2. washThe organic fractions were combined washed with water (3×350 ml), brine (250 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified on
  7. washsilica (300 g) eluting with ethyl acetate:hexane (3:1)

Quellen und Nachweise

ORD-Eintrag
ord-9a18c8c753594ef6ac9d3248bad502fd
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06610518B2

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