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Potassium Carbonate → ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate

HRID 1169355
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1169355
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[CH3:16][C:17]1[CH:22]=[CH:21][C:20](OB(O)O)=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>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.C1(C)C=CC=CC=1.C(O)C.O>[CH3:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:10]=[C:9]3[C:5]([CH:6]=[C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[NH:8]3)=[CH:4][CH:3]=2)=[CH:19][CH:18]=1
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Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 70094966-Bromo-1H-indole-2-carboxylic acid ethyl esterHCID 190353504-Methylphenyl dihydrogen borate

Produkt 1

HCID 22990151ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylateAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

A mixture of ethyl 6-bromo-1H-indole-2-carboxylate (2.5 g) and 4-methylphenylboric acid (1.39 g), potassium carbonate (2.58 g) and toluene/ethanol/water (90/9/9 ml) was stirred at room temperature for one hour. Into the reaction mixture was added tetrakis(triphenylphosphine)palladium (0.32 g), and the resulting mixture was heated at reflux for 18 hours. After cooling to room temperature, the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the residue was subjected to purification using column chromatography (ethyl acetate/hexane 1:5→1:2→1:1) and to recrystallization (ethyl acetate/hexane) to obtain ethyl 6-(4-methylphenyl)-1H-indole-2-carboxylate (1.92 g) as colorless crystals.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 18 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  6. dry with materialwas dried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was subjected to purification
  9. customto recrystallization (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-09fb8bc2a9b44f5e965601581d9830ee
Quelldatensatz
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06627651B1

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