Acetic Acid → 2-[[[(1-{6-[(2,2-Dichlorocyclopropyl)methoxy]-5-fluoro-1-methylindazol-3-yl}ethylidene)amino]oxy]methyl]-alpha-(methoxymethylene)phenylacetic Acid Methyl Ester

HRID 1584714

Reaktionsgleichung

Reaktionsgleichung von HRID 1584714
[Cl:1][C:2]1([Cl:22])[CH2:4][CH:3]1[CH2:5][O:6][C:7]1[CH:15]=[C:14]2[C:10]([C:11]([C:17](=[N:19][OH:20])[CH3:18])=[N:12][N:13]2[CH3:16])=[CH:9][C:8]=1[F:21].[H-].[Na+].[CH3:25][O:26][C:27](=[O:40])[C:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38]Br)=[CH:29][O:30][CH3:31].C(O)(=O)C>CN(C)C=O>[CH3:25][O:26][C:27](=[O:40])[C:28]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][O:20][N:19]=[C:17]([C:11]1[C:10]2[C:14](=[CH:15][C:7]([O:6][CH2:5][CH:3]3[CH2:4][C:2]3([Cl:1])[Cl:22])=[C:8]([F:21])[CH:9]=2)[N:13]([CH3:16])[N:12]=1)[CH3:18])=[CH:29][O:30][CH3:31]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 53395349Methyl 2-[2-(bromomethyl)phenyl]-3-methoxyprop-2-enoateHCID 136340728HCID 136340728, Verbindung

Produkt 1

HCID 867543822-[[[(1-{6-[(2,2-Dichlorocyclopropyl)methoxy]-5-fluoro-1-methylindazol-3-yl}ethylidene)amino]oxy]methyl]-alpha-(methoxymethylene)phenylacetic Acid Methyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

A solution of 0.9 g of 1-[6-(2,2-dichlorocyclopropylmethoxy)-5-fluoro-1-methyl-1H-indazol-3-yl]-ethanone oxime in 10 ml of N,N-dimethylformamide is added dropwise to a suspension of 0.2 g of sodium hydride in 15 ml of N,N-dimethylformamide and the reaction mixture is stirred at room temperature for 15 minutes. Then 1.04 g of 2-(α-bromo-o-tolyl)-3-methoxyacrylic acid methyl ester in 10 ml of N,N-dimethylformamide are added dropwise and the reaction mixture is stirred at room temperature for a further 3 hours. The mixture is then acidified with acetic acid and concentrated by evaporation in vacuo at approx. 50° C. The residue is dissolved in ethyl acetate and the solution is washed twice with water and once with saturated sodium chloride solution, dried with sodium sulfate and concentrated by evaporation in vacuo. Purification by flash chromatography (silica gel, ethyl acetate/hexane 1:1) yields the title compound having a melting point of 138-140° C.

Aufarbeitung

  1. stirringthe reaction mixture is stirred at room temperature for a further 3 hours
  2. concentrationconcentrated by evaporation in vacuo at approx. 50° C
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washthe solution is washed twice with water and once with saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated by evaporation in vacuo
  7. customPurification by flash chromatography (silica gel, ethyl acetate/hexane 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-e38432dbd68c4e1d87c34b8cdedadc95
Quelldatensatz
uspto-grants-1999_08
Patentnummer
US05935908

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