Dimethylformamide → HCID 69670779, Verbindung

HRID 1191672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191672
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9][CH3:10])=[CH:4][C:3]=1[CH2:11][CH:12](O)[CH:13]([CH3:16])[CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].BrC1C(C)=CC(C)=CC=1C.CN(C)C=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:11]=[C:12]([CH:13]([CH3:16])[CH2:14][CH3:15])[NH:1]2)=[CH:4][C:5]=1[O:9][CH3:10]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 684732-BromomesityleneHCID 696710981-(2-Amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol

Produkt 1

HCID 69670779HCID 69670779, VerbindungAusbeute 92,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

A mixture of 1-(2-amino-4-chloro-5-methoxyphenyl)-3-methylpentan-2-ol (602 mg), tetrakis(triphenylphosphine)palladium (0) (135 mg), potassium carbonate (646 mg), 2-bromomesitylene (0.420 mL) and N,N-dimethylformamide (11.7 mL) was stirred at 160° C. for one hour under microwave irradiation. The reaction mixture was allowed to cool to ambient temperature. Water was added to the reaction mixture and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (514 mg).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. extractionthis resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-104e9aaa8fe846078490ac4f57996a64
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680120B2

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