Water → HCID 57930893, Verbindung

HRID 1096985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1096985
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([O:15][CH3:16])[C:13]=1Br)[C:7]([O:9][CH3:10])=[O:8])[CH3:2].[CH3:17][N:18]1[CH:22]=[C:21](B2OC(C)(C)C(C)(C)O2)[CH:20]=[N:19]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>COCCOC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([O:15][CH3:16])[C:13]=1[C:21]1[CH:20]=[N:19][N:18]([CH3:17])[CH:22]=1)[C:7]([O:9][CH3:10])=[O:8])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57930995HCID 57930995, Verbindung

Produkt 1

HCID 57930893HCID 57930893, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Methyl 3-ethoxy-4-bromo-5-methoxybenzoate (300 mg) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (324 mg) were dissolved in DME in a nitrogen atmosphere, and potassium phosphate (661 mg) and 1,1′-bis(diphenylphosphino)ferrocene palladium(II) chloride-CH2Cl2 complex (85 mg) were added to it at room temperature and degassed. The reaction liquid was stirred overnight at 90° C., then cooled to room temperature, water was added to it, and filtered through Celite. The filtrate was extracted with chloroform, washed with saturated saline water, and dried with sodium sulfate. Sodium sulfate was removed through filtration, the filtrate was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 40/60) to obtain the title compound as a white solid.

Aufarbeitung

  1. additionwere added to it at room temperature
  2. customdegassed
  3. customThe reaction liquid
  4. temperaturecooled to room temperature
  5. filtrationfiltered through Celite
  6. extractionThe filtrate was extracted with chloroform
  7. washwashed with saturated saline water
  8. dry with materialdried with sodium sulfate
  9. customSodium sulfate was removed through filtration
  10. concentrationthe filtrate was concentrated under reduced pressure
  11. customthe residue was purified through silica gel column chromatography (hexane/ethyl acetate=100/0 to 40/60)

Quellen und Nachweise

ORD-Eintrag
ord-915960f14e944017bedbde8b38959a69
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08138197B2

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