Water → 7-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone

HRID 21101

Reaktionsgleichung

Reaktionsgleichung von HRID 21101
[NH2:1][C:2]1[CH:3]=[CH:4][C:5](Br)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2.[C:13](=[O:16])([O-])[O-].[K+].[K+].[OH2:19]>>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:2]2[CH:3]=[CH:4][C:5]([OH:19])=[C:6]([O:16][CH3:13])[CH:10]=2)=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Komponenten

4

Edukt 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 197019327-Amino-4-bromo-2,3-dihydroisoindol-1-one

Produkt 1

HCID 684876617-Amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinoneAusbeute 94 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

7-Amino-4-bromoisoindolinone (150 mg, 0.661 mmol) was dissolved in dimethoxythane (10.5 mL), and the solution was added with 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenol (331 mg, 1.32 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (43.2 mg, 0.0529 mmol) and potassium carbonate (456 mg, 3.31 mmol), and stirred at 90° C. for 4.3 hours under argon atmosphere. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=4/1, chloroform/methanol=10/1) to obtain 7-amino-4-(4-hydroxy-3-methoxyphenyl)isoindolinone (169 mg, yield 94%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative thin-layer chromatography (chloroform/acetonitrile=4/1, chloroform/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-f23a68453a6c4b1fa08a3092beab187e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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