Sodium hydride → HCID 86700759, Verbindung

HRID 2272550Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2272550
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:11])=[CH:5][NH:6]2.[H-].[Na+].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>CN(C)C=O>[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH3:11])=[CH:5][N:6]2[CH2:20][C:19]1[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 529877044-Bromo-3-methyl-1H-indole

Produkt 1

HCID 86700759HCID 86700759, VerbindungAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

4-Bromo-3-methyl-1H-indole (1.33 g) was dissolved in dimethylformamide (20 mL), and sodium hydride (0.33 g) was added thereto under ice-cooling. After stirring at 0° C. for 15 minutes, p-methoxybenzyl chloride (0.95 mL) was added thereto. The reaction solution was stirred under heating at 70° C. for 30 minutes and partitioned between ethyl acetate and 1M HCl aqueous solution. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate) to obtain compound (45a) (2.09 g, 99%) as a colorless oily substance.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. stirringThe reaction solution was stirred
  3. temperatureunder heating at 70° C. for 30 minutes
  4. custompartitioned between ethyl acetate and 1M HCl aqueous solution
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. customby evaporation
  9. customthe residue was purified by neutral silica gel column chromatography (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-62e5f13f368147e08a291525d54f4e8a
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120780B2

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