Toluene → HCID 70654352, Verbindung

HRID 539492

Reaktionsgleichung

Reaktionsgleichung von HRID 539492
Br[C:2]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:3]=1[C:4]#[N:5].CC1(C)C(C)(C)OB([C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[NH2:22])O1.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:11][O:10][C:7]1[CH:8]=[CH:9][C:2]2[C:3](=[C:4]([NH2:5])[N:22]=[C:21]3[C:20]=2[CH:26]=[CH:25][CH:24]=[CH:23]3)[CH:6]=1

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 27346522-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 217840962-Bromo-5-methoxybenzonitrileHCID 22031701Potassium phosphate, tribasic, monohydrate

Produkt 1

HCID 70654352HCID 70654352, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

2-Bromo-5-methoxybenzonitrile (1.32 g, 6.23 mmol), 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.36 g, 6.23 mmol), bis(triphenylphosphine)palladiumdichloride (0.437 g, 0.623 mmol) and potassium phosphate monohydrate (4.30 g, 18.68 mmol) were added to toluene (30 mL) and water (3 mL). The reaction mixture was degassed with bubbled nitrogen gas for 30 minutes before being refluxed under nitrogen for 15 h. After cooling, the reaction mixture was filtered through Celite® and the organic layer was extracted with ethyl acetate. After removal of the solvents, the crude material was triturated with 40 mL of DCM followed by 50 mL of hexanes to give 8-methoxyphenanthridin-6-amine (0.95 g, 68%) as a light yellow solid. The product was confirmed by GC/MS and NMR.

Aufarbeitung

  1. customThe reaction mixture was degassed with bubbled nitrogen gas for 30 minutes
  2. temperaturebefore being refluxed under nitrogen for 15 h
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered through Celite®
  5. extractionthe organic layer was extracted with ethyl acetate
  6. customAfter removal of the solvents
  7. customthe crude material was triturated with 40 mL of DCM

Quellen und Nachweise

ORD-Eintrag
ord-64e2c143a486468fb1914509aa94df46
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871361B2

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