1-Methyl-3-(trifluoroacetyl)-1H-indole → HCID 59437212, Verbindung

HRID 244465

Reaktionsgleichung

Reaktionsgleichung von HRID 244465
Br[C:2]1[CH:19]=[CH:18][C:5]2[N:6]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:7](=[O:10])[N:8]([CH3:9])[C:4]=2[CH:3]=1.C([Li])(C)(C)C.[F:25][C:26]([F:40])([F:39])[C:27]([C:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]([CH3:38])[CH:30]=1)=[O:28]>C1COCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([N:6]2[C:5]3[CH:18]=[CH:19][C:2]([C:27]([OH:28])([C:29]4[C:37]5[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=5)[N:31]([CH3:38])[CH:30]=4)[C:26]([F:25])([F:40])[F:39])=[CH:3][C:4]=3[N:8]([CH3:9])[C:7]2=[O:10])=[CH:12][CH:13]=1

Komponenten

5

Edukt 3

HCID 35243881-Methyl-3-(trifluoroacetyl)-1H-indoleHCID 59437286HCID 59437286, VerbindungHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 59437212HCID 59437212, VerbindungAusbeute 12,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a chilled (−78° C.) solution of 5-bromo-1-(4-fluorophenyl)-3-methyl-1,3-dihydro-benzimidazol-2-one (80 mg, 0.25 mmol) in anhydrous THF (3 mL) was added tert-butyllithium (0.2 mL of 1.7 M solution in heptane, 0.34 mmol). After 1 minute, a chilled (−78° C.) solution of 2,2,2-trifluoro-1-(1-methyl-1H-indol-3-yl)ethanone (57 mg, 0.25 mmol) in anhydrous THF (1 mL) was added. After 10 minutes, the mixture was quenched with ammonium chloride solution and extracted with three 15 mL portions of methylene chloride. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to afford a brownish oil. The residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride to afford 15 mg of the title compound as a white powder. MS m/z 470 (MH+).

Aufarbeitung

  1. additionwas added
  2. waitAfter 10 minutes
  3. customthe mixture was quenched with ammonium chloride solution
  4. extractionextracted with three 15 mL portions of methylene chloride
  5. washThe combined organic layers were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto afford a brownish oil
  9. customThe residue was purified by column chromatography over silica gel eluting with 0-10% ethyl acetate in methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-b80428248671469ab8751842b05dafcb
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658637B2

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