Sodium hydride → Ethyl 4-bromo-6-fluoro-2-(methoxycarbonyl)-1H-indole-1-butanoate

HRID 857421

Reaktionsgleichung

Reaktionsgleichung von HRID 857421
[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[NH:6]2.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23].[NH4+].[Cl-]>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[N:6]2[CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 76300Ethyl 4-bromobutyrateHCID 21867463Methyl 4-bromo-6-fluoro-1H-indole-2-carboxylate

Produkt 1

HCID 21867557Ethyl 4-bromo-6-fluoro-2-(methoxycarbonyl)-1H-indole-1-butanoateAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 4-bromo-6-fluoro-1H-indole-2-carboxylate (10 g, 36.8 mmol) in DMF (100 mL) at 0° C. was added NaH (1.8 g, 44.2 mmol, 60% in oil). The mixture was stirred at r.t. for 30 minutes and tetra-n-butylammonium iodide (500 mg) was added, followed by the addition of ethyl 4-bromobutyrate (10.1 g, 51.5 mmol). The reaction mixture was stirred at r.t. for 3 h, poured into saturated aqueous NH4Cl and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc to give 13.2 g of the title compound.

Aufarbeitung

  1. stirringThe reaction mixture was stirred at r.t. for 3 h
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluted with 20% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-1cb1a896013746d3859385f2d7568f03
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07144913B2

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