Potassium Carbonate → Diethyl 2-bromo-2-(indol-4-yloxy)malonate

HRID 16565

Reaktionsgleichung

Reaktionsgleichung von HRID 16565
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>CC(C)=O>[Br:17][C:18]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20].[NH:6]1[C:7]2[C:3](=[C:2]([O:1][CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:5]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 69637Diethyl bromomalonate2×HCID 754211H-indol-4-ol

Produkt 2

HCID 11608989Diethyl 2-(indol-4-yloxy)malonateAusbeute 21 %HCID 11639270Diethyl 2-bromo-2-(indol-4-yloxy)malonateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

A solution of 4-hydroxyindole (266 mg, 2 mmol) in acetone (20 mL) was cooled to 0° C. under nitrogen and anhydrous potassium carbonate (414 mg, 3 mmol) was added. A solution of commercial diethyl bromomalonate (92%; 520 mg, 2 mmol) in acetone (20 mL) was added dropwise. After stirring for 5 h at room temperature, more diethyl bromomalonate (92%; 520 mg) was added and the mixture was stirred at room temperature overnight. Work up and flash chromatography as above afforded 7 (360 mg, 45%) and 8 (123 mg, 21%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight

Quellen und Nachweise

ORD-Eintrag
ord-048ee2c07d0f4ab183f06fcc23ac2876
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737169B2

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