Sodium Bicarbonate → 1-Acetyl-2,3-dihydro-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrile

HRID 273854Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 273854
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH2:18])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[O:29][CH2:30][C:31]([F:34])([F:33])[F:32].C(=O)(O)[O-].[Na+]>C(O)C>[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:15][CH:16]([NH:18][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH2:30][C:31]([F:32])([F:33])[F:34])[CH3:17])=[CH:10][C:11]=2[C:13]#[N:14])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 200943331-Acetyl-5-(2-aminopropyl)-2,3-dihydro-1H-indole-7-carbonitrileHCID 200943351-(2-Bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene

Produkt 1

HCID 200943401-Acetyl-2,3-dihydro-5-[2-[[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl]amino]propyl]-1H-indole-7-carbonitrileAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-acetyl-5-(2-aminopropyl)indoline-7-carbonitrile (1.37 g) and 1-(2-bromoethoxy)-2-(2,2,2-trifluoroethoxy)benzene (1.50 g) in ethanol (6 ml) was added sodium bicarbonate (0.47 g), and the mixture was reacted in a sealed tube at 95° C. for 12 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent, and recrystallized from diethyl ether-hexane to give 1.30 g of 1-acetyl-5-[2-[2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethylamino]propyl]indoline-7-carbonitrile melting at 64°-65° C.

Aufarbeitung

  1. customthe mixture was reacted in a sealed tube at 95° C. for 12 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  4. additiona mixture of methylene chloride, diethyl ether and methanol (5/5/1) as eluent
  5. customrecrystallized from diethyl ether-hexane

Quellen und Nachweise

ORD-Eintrag
ord-1cee60b0311d4c5f8ca5695401856b11
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05387603

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