Acetonitrile → 1-(2-diethylamino-ethyl)-2,3-dihydro-1H-indol-5-ylamine

HRID 898526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898526
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1Cl.[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13].[C:19](#[N:21])[CH3:20]>[Cu]I>[CH2:12]([N:14]([CH2:17][CH3:18])[CH2:15][CH2:16][N:21]1[C:2]2[C:3](=[CH:4][C:5]([NH2:8])=[CH:6][CH:7]=2)[CH2:20][CH2:19]1)[CH3:13]

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 346671-Bromo-2-chloro-4-nitrobenzene

Produkt 1

HCID 284189531-(2-diethylamino-ethyl)-2,3-dihydro-1H-indol-5-ylamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Versuchsvorschrift

Under a nitrogen atmosphere 12.5 mL (0.090 mol) of 3-N,N-diethylamino-propyne was added to 25.00 g (0.106 mol) of 4-bromo-3-chloro-nitrobenzene, 43.7 mL (0.315 mol) of triethylamine, 10.40 g (0.009 mol) of tetrakis[triphenylphosphine]-palladium(II) and 1.71 g (0.009 mol) of copper(I)-iodide in 250 mL acetonitrile and the mixture was refluxed for 18 hours. The reaction mixture was evaporated down i. vac., combined with EtOAc and the organic phase was washed with water. The org. phase was evaporated down i. vac. and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10:0→4:1) followed by column chromatography (silica gel, dichloromethane).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 18 hours
  2. customThe reaction mixture was evaporated down i
  3. washthe organic phase was washed with water
  4. customphase was evaporated down i
  5. customand the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10:0→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-6b503742cda149c79f0bc141fe7bb514
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351719B2

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