Toluene → 6-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

HRID 513846

Reaktionsgleichung

Reaktionsgleichung von HRID 513846
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9](Br)[CH:8]=2)=[O:4].[CH3:25][C:26](P(C(C)(C)C)C1C=CC=CC=1)([CH3:28])C.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([CH:28]1[CH2:26][CH2:25]1)[CH:8]=2)=[O:4]

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 316378Di-tert-butylphenylphosphineHCID 680048106-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

Produkt 1

HCID 680048306-cyclopropyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Predetermined amounts of 6-bromo-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid methyl ester (300 mg, 0.73 mmol), palladium acetate (16.5 mg, 0.07 mmol), bis(1,1-dimethylethyl)phenylphosphine (0.028 ml, 0.12 mmol), potassium cyclopropyl trifluoro borate (163 mg, 1.1 mmol), and cesium carbonate (718 mg, 2.2 mmol) were placed in a reaction container, and toluene (5 ml) and water (0.5 ml) were added thereto. The resulting mixture was then stirred at 100° C. for 14 hours. After cooling it to room temperature, the mixture was diluted with ethyl acetate, and washed twice with water, and then dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and concentration was performed. Then, the residue obtained by concentration under reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3). Thus, a yellow solid was obtained (208 mg, 77%).

Aufarbeitung

  1. additionwere added
  2. temperatureAfter cooling it to room temperature
  3. washwashed twice with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe desiccant was removed by filtration, and concentration
  6. customThen, the residue obtained by concentration under reduced pressure
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=97/3 to 7/3)
  8. customThus, a yellow solid was obtained (208 mg, 77%)

Quellen und Nachweise

ORD-Eintrag
ord-b73532bf65374dffad1e8f116518cd41
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102692B2

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