Potassium Carbonate → 1-benzenesulfonyl-3-(3,4-dimethoxy-phenyl)-1H-indole

HRID 1820880

Reaktionsgleichung

[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](Br)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[CH:26][C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.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>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:25]3[CH:24]=[CH:23][C:22]([O:21][CH3:20])=[C:27]([O:28][CH3:29])[CH:26]=3)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

1-Benzenesulfonyl-3-bromoindole 20 (350 mg, 1.0 mmol) was dissolved in tetrahydrofuran (6 mL). Into the solution was added 3,4-dimethoxyphenyl boronic acid (379 mg, 2.1 mmol), tetrakis(triphenylphosphine)palladium(0) (60 mg, 0.05 mmol) and 1 M potassium carbonate (3 mL). The reaction mixture was heated in a CEM Discover microwave instrument at 120° C. for 10 minutes. The reaction mixture was concentrated under reduced pressure and partioned between ethyl acetate and saturated sodium bicabonate. The organic portion was dried over anhydrous magnesium sulfate, and filtered. The filtrate was adsorbed onto silica gel and purified by flash chromatography (5%-50% ethyl acetate:hexanes) to provide the desired product, 19, (359 mg, 88%).

Aufarbeitung

concentrationThe reaction mixture was concentrated under reduced pressure
dry with materialThe organic portion was dried over anhydrous magnesium sulfate
filtrationfiltered
custompurified by flash chromatography (5%-50% ethyl acetate:hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-915151a8ef954ae7b85b773df75a1584
Quelldatensatz: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07605168B2

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