Potassium Carbonate → 7-Amino-2,3-dihydro-1H-isoindol-1-one

HRID 21189

Reaktionsgleichung

Reaktionsgleichung von HRID 21189
[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.CB1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].NC1C=CC(C)=C2C=1C(=O)NC2>C(COC)OC.O>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[NH:8][CH2:7]2

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 197019327-Amino-4-bromo-2,3-dihydroisoindol-1-oneHCID 534386827-Amino-4-methylisoindolin-1-one

Produkt 1

HCID 162289237-Amino-2,3-dihydro-1H-isoindol-1-oneAusbeute 96,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Example 152, 7-amino-4-bromoisoindolinone (100 mg, 0.440 mmol) was dissolved in dimethoxyethane (5 mL), and the solution was treated with trimethylboroxine (0.184 mL, 1.76 mmol), [bis(diphenylphosphino)ferrocene]dichloropalladium (28.7 mg, 0.0352 mmol), potassium carbonate (304 mg, 2.20 mmol) and water (0.158 mL), followed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=4/1) to obtain a mixture of 7-amino-4-methylisoindolinone and 7-aminoisoindolinone (62.9 mg, ratio 10/1, yield 89%).

Aufarbeitung

  1. customfollowed by purification by preparative thin-layer chromatography (chloroform/acetonitrile=4/1)
  2. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-bfebba25684b45fbb890436a5a086c39
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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