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1-Chloro-4-(chloromethyl)benzene → Methyl alpha-[N-methyl-3-(trifluoromethyl)benzylamino]-1-(4-chlorobenzyl)indole-3-acetate

HRID 5611
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 5611
[H-].[Na+].[F:3][C:4]([F:28])([F:27])[C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[CH2:8][NH:9][CH:10]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1.[CH3:38]CCCCC.C(OCC)(=O)C>CN(C)C=O.CCOCC>[CH3:38][N:9]([CH2:8][C:7]1[CH:24]=[CH:25][CH:26]=[C:5]([C:4]([F:3])([F:27])[F:28])[CH:6]=1)[CH:10]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:34][C:33]2[CH:36]=[CH:37][C:30]([Cl:29])=[CH:31][CH:32]=2)[CH:16]=1)[C:11]([O:13][CH3:14])=[O:12]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 19796632Methyl alpha-[3-(trifluoromethyl)benzylamino]-indole-3acetateHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 19796715Methyl alpha-[N-methyl-3-(trifluoromethyl)benzylamino]-1-(4-chlorobenzyl)indole-3-acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a magnetically stirred suspension of sodium hydride (60% oil dispersion washed two times with hexane, 80 mg, 2.0 mmol) in 5 mL of dimethylformamide (DMF) under nitrogen was added methyl α-[3-(trifluoromethyl)benzylamino]-indole-3acetate (752 mg, 2.0 mmol) dissolved in 2 mL DMF. Stirring was continued at room temperature for 10 minutes. At the end of this time, 0.322 g (2.0 mmol) of parachlorobenzyl chloride was added and the reaction stirred at room temperature for one hour. The reaction was diluted with ether and the ether solution was washed two times with water. The ether extract was then washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product. Flash chromatography of the crude product with 100 g of silica gel and using hexane-ethyl acetate (4:10) as the eluent afforded 419 mg of the title compound.

Aufarbeitung

  1. stirringthe reaction stirred at room temperature for one hour
  2. washthe ether solution was washed two times with water
  3. extractionThe ether extract
  4. washwas then washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give the crude product

Quellen und Nachweise

ORD-Eintrag
ord-3f8581bc16ea4d41a3c766acc9b0ade0
Quelldatensatz
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05245046

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