Potassium Carbonate → HCID 86681614, Verbindung

HRID 571195

Reaktionsgleichung

Reaktionsgleichung von HRID 571195
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-:3])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][C:21]([O:23][CH3:24])=[O:22]>CC#N>[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[N:11]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:10]=[CH:9]2)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 233967-NitroindoleHCID 60984Methyl bromoacetate2×

Produkt 1

HCID 86681614HCID 86681614, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 7-nitro-1H-indole (0.5 g, 3.08 mmol) in dry CH3CN (20 ml), K2CO3 (0.511 g, 3.70 mmol) was added at room temperature. After 10 minutes, methyl 2-bromoacetate (0.343 ml, 3.70 mmol) was added dropwise, and the reaction was refluxed for 24 hours. Additional K2CO3 (0.511 g, 3.70 mmol) and methyl 2-bromoacetate (0.343 ml, 3.70 mmol) were added, and the stirring was prolonged for further 16 hours. The reaction was cooled at room temperature and the solvent was evaporated under vacuum. The resulting crude was partitioned between water and DCM; the organic phase was dried over sodium sulfate and evaporated under vacuum. The crude was purified by flash column chromatography on silica gel (hexane:ethyl acetate=9:1) affording methyl 2-(7-nitro-1H-indol-1-yl)acetate that crystallizes on standing (0.37 g, 1.580 mmol, 51% yield). MS/ESI+ 234.9 [MH]+.

Aufarbeitung

  1. temperaturethe reaction was refluxed for 24 hours
  2. waitthe stirring was prolonged for further 16 hours
  3. customthe solvent was evaporated under vacuum
  4. customThe resulting crude was partitioned between water and DCM
  5. dry with materialthe organic phase was dried over sodium sulfate
  6. customevaporated under vacuum
  7. customThe crude was purified by flash column chromatography on silica gel (hexane:ethyl acetate=9:1)

Quellen und Nachweise

ORD-Eintrag
ord-3b88eb2600b1460fb4224f3d9fb5ecd4
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09024027B2

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