Sodium hydride → HCID 69670750, Verbindung

HRID 1191674Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1191674
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5]2.[H-].[Na+].Cl[CH2:20][C:21]1[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:20][C:21]1[N:26]=[C:25]([C:27]([O:29][CH3:30])=[O:28])[CH:24]=[CH:23][CH:22]=1)[C:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:5]2

Komponenten

8

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 14814655-chloro-2-phenyl-1H-indoleHCID 53404482Methyl 6-(chloromethyl)pyridine-2-carboxylate

Produkt 1

HCID 69670750HCID 69670750, VerbindungAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-2-phenylindole (154 mg) in N,N-dimethylformamide (1.5 mL) was added sodium hydride (dispersed in liquid paraffin, minimum 55%, 31 mg) at room temperature, and the mixture was stirred for 15 minutes. Methyl 6-(chloromethyl)pyridine-2-carboxylate (126 mg) was added and this resulting mixture was stirred at 50 to 60° C. for additional 18 hours. Water, ethyl acetate and a saturated aqueous ammonium chloride solution were added to the reaction mixture. The organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed successively with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (112 mg).

Aufarbeitung

  1. stirringthis resulting mixture was stirred at 50 to 60° C. for additional 18 hours
  2. customThe organic layer was separated
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layers were washed successively with water and saturated saline
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ba4fac05a14641eeb84c9286189379f4
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680120B2

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