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Sodium hydride → 1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole

HRID 1191650
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1191650
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:6]2.[H-].[Na+].[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O.O>[CH2:20]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][N:8]1[C:9]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=2)[CH:6]=[C:7]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 2928505-Methoxy-2-phenylindoleHCID 15020473-Benzyloxybenzyl bromide

Produkt 1

HCID 696710521-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindoleAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 5-methoxy-2-phenylindole (245 mg) in N,N-dimethylformamide (4.5 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 72 mg) under cooling with ice, and the mixture was stirred at room temperature for 75 minutes. Then a solution of 3-(benzyloxy)benzyl bromide (365 mg) in N,N-dimethylformamide (1 mL) was added dropwise, and the mixture was stirred at 80° C. for 15 hours. The reaction mixture was cooled to room temperature. A saturated aqueous ammonium chloride solution-water (2/1) were added and this resulting mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography to obtain the title compound (202 mg).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at 80° C. for 15 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionthis resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by aminopropylated silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a5c0a6f9c6fa4576879e49b61502fcdb
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680120B2

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