Trimethylamine → (2E)-1-(7-bromo-1-methylindol-2-yl)-2-hydrazinylideneethanone

HRID 12622

Reaktionsgleichung

Reaktionsgleichung von HRID 12622
C[Si]([CH:5]=[N+:6]=[N-:7])(C)C.CN(C)C.[Br:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH3:22])[C:19]([C:23](Cl)=[O:24])=[CH:18]2.[Cl-].[NH4+]>O1CCCC1.C(#N)C>[Br:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[N:20]([CH3:22])[C:19]([C:23](=[O:24])/[CH:5]=[N:6]/[NH2:7])=[CH:18]2

Komponenten

7

Edukt 4

HCID 1146TrimethylamineHCID 25517Ammonium ChlorideHCID 167693TrimethylsilyldiazomethaneHCID 875414197-bromo-1-methyl-1H-indole-2-carboxylic acid chloride

Produkt 1

HCID 145729974(2E)-1-(7-bromo-1-methylindol-2-yl)-2-hydrazinylideneethanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a dichloromethane (2 mL) solution of 7-bromo-1-methyl-1H-indole-2-carboxylic acid (200 mg), oxalyl dichloride (0.10 mL) and N,N-dimethylformamide (5 mL) were added and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated, azeotroped twice with toluene to obtain a crude product of 7-bromo-1-methyl-1H-indole-2-carboxylic acid chloride. Separately, a solution was prepared by dissolving 2M trimethylsilyldiazomethane (0.60 mL) and trimethylamine (0.16 mL) in tetrahydrofuran (2 mL)-acetonitrile (2 mL) and a tetrahydrofuran (1 mL)acetonitrile (1 mL) solution of 7-bromo-1-methyl-1H-indole-2-carboxylic acid chloride was added thereto, and then the mixture was stirred at room temperature for 4 hours. To the reaction mixture, an aqueous saturated ammonium chloride solution was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate and then concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 85:15) to obtain the titled compound having the following physical properties (72 mg).

Aufarbeitung

  1. customSeparately, a solution was prepared
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=90:10 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-757e66c04e504a789c6f1879b02fcaff
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728023B2

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