Methyl iodide → Methyl-4-(5-iodoindazole-1-yl)-benzoate

HRID 13139

Reaktionsgleichung

Reaktionsgleichung von HRID 13139
[C:1]([O-])([O-])=O.[K+].[K+].[I:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)[N:12]=[CH:11]2.CI>CN(C=O)C>[CH3:1][O:22][C:21](=[O:23])[C:20]1[CH:19]=[CH:18][C:17]([N:13]2[C:14]3[C:10](=[CH:9][C:8]([I:7])=[CH:16][CH:15]=3)[CH:11]=[N:12]2)=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 593397454-(5-Iodoindazole-1-yl)-benzoic acid

Produkt 1

HCID 66812731Methyl-4-(5-iodoindazole-1-yl)-benzoateAusbeute 76,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

K2CO3 (7.35 g, 53.2 mmol) is suspended in 110 mL DMF. 4-(5-iodoindazole-1-yl)-benzoic acid (17.6 g, 48.33 mmol), dissolved in 25 mL DMF, is added dropwise. The reaction mixture is stirred for 30 min at r.t. Subsequently CH3I (3.31 mL, 53.2 mmol) is added dropwise (temperature rises to 30° C.). The reaction mixture is stirred overnight at r.t. and then poured on ice water. It is three times extracted with ethyl acetate. The combined organic extracts are washed twice with water and brine. After drying over Na2SO4 and filtration the solvent is evaporated. The residue is purified by chromatography (silicagel, eluents: ethyl acetate/hexane) yielding 14.03 g (76.8%) of the title compound.

Aufarbeitung

  1. additionis added dropwise
  2. stirringThe reaction mixture is stirred overnight at r.t.
  3. additionpoured on ice water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts are washed twice with water and brine
  6. dry with materialAfter drying over Na2SO4 and filtration the solvent
  7. customis evaporated
  8. customThe residue is purified by chromatography (silicagel, eluents: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-4339b0ab9d0b40d582cb4138a77dda1e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728030B2

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