Trifluoroacetic acid → (E)-N-(2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-en-1-yl)-1H-indol-1-yl)-2-oxoethyl)-3,3,3-trifluoropropanamide

HRID 587231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 587231
NCC(N1C2C(=CC(/C=C/[CH:16](C3C=C(Cl)C(F)=C(Cl)C=3)[C:17]([F:20])([F:19])[F:18])=CC=2)C=C1)=O.[Cl:30][C:31]1[CH:32]=[C:33]([CH:39]([C:62]([F:65])([F:64])[F:63])/[CH:40]=[CH:41]/[C:42]2[CH:43]=[C:44]3[C:48](=[CH:49][CH:50]=2)[N:47]([C:51](=[O:61])[CH2:52][NH:53][C:54](=[O:60])OC(C)(C)C)[CH:46]=[CH:45]3)[CH:34]=[C:35]([Cl:38])[C:36]=1[F:37].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:30][C:31]1[CH:32]=[C:33]([CH:39]([C:62]([F:65])([F:63])[F:64])/[CH:40]=[CH:41]/[C:42]2[CH:43]=[C:44]3[C:48](=[CH:49][CH:50]=2)[N:47]([C:51](=[O:61])[CH2:52][NH:53][C:54](=[O:60])[CH2:16][C:17]([F:20])([F:19])[F:18])[CH:46]=[CH:45]3)[CH:34]=[C:35]([Cl:38])[C:36]=1[F:37]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 86675170(E)-2-amino-1-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)ethanoneHCID 86675171(E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate

Produkt 1

HCID 86675172(E)-N-(2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-en-1-yl)-1H-indol-1-yl)-2-oxoethyl)-3,3,3-trifluoropropanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

(E)-2-Amino-1-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)ethanone (BI23): To a stirred solution of (E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate (0.05 g, 0.09 mmol) in CH2Cl2 (5.0 mL) was added TFA (0.01 mL) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 solution, water and brine solution. The separated CH2Cl2 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude title compound which was used in the next step without further purification (50 mg).

Aufarbeitung

  1. washwashed with saturated NaHCO3 solution, water and brine solution
  2. dry with materialThe separated CH2Cl2 layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7040d6160d2a4c35af9dfcdf028fa010
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09226500B2

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