1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent] → 4-[2-carbamoyl-3-fluoro-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 18198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 18198
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[CH:16]=[C:17]([C:31](=[O:33])[NH2:32])[N:18]3[CH2:23][C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]S(C(F)(F)[F:39])(=O)=O.F[N+]1C(C)=CC(C)=CC=1C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:15]=2[C:16]([F:39])=[C:17]([C:31](=[O:33])[NH2:32])[N:18]3[CH2:23][C:24]2[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 27245751-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate [Fluorinating Reagent]HCID 59344902HCID 59344902, Verbindung

Produkt 1

HCID 593449184-[2-carbamoyl-3-fluoro-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl esterAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-[2-Carbamoyl-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.0155 gm, 0.034 mmol) was dissolved in dichloromethane and 1-fluoro-2,4,6-trimethylpyridinium triflate (85%, 0.012 gm, 0.035 mmol) was added and the reaction mixture was stirred at room temperature overnight. The mixture was transferred onto two preparative thin layer chromatography plates and eluted with 1/1 ethyl acetate/hexane, then further purified on two analytical thin layer chromatography plates (1/1 ethyl acetate/hexane), and then additionally purified on two more analytical plates (35/65 ethyl acetate/hexane) to give 4-[2-carbamoyl-3-fluoro-1-(4-fluoro-benzyl)-1H-indol-4-yl]-piperazine-1-carboxylic acid tert-butyl ester (0.009 gm, 56% yield).

Aufarbeitung

  1. washeluted with 1/1 ethyl acetate/hexane
  2. customfurther purified on two analytical thin layer chromatography plates (1/1 ethyl acetate/hexane)
  3. customadditionally purified on two more analytical plates (35/65 ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-5273fb302fec4087ac4dbb737e7d1db6
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741326B2

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