Sodium hydride → 2-[1-(12-Bromo-dodecyl)-2-methyl-1H-indol-4-yloxy]-3-methylbutyric acid ethyl ester

HRID 1445890

Reaktionsgleichung

Reaktionsgleichung von HRID 1445890
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:22])[CH:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH3:21])[NH:16]2)[CH:8]([CH3:10])[CH3:9])[CH3:4].[Br:23][CH:24](Br)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:5][C:6](=[O:22])[CH:7]([O:11][C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[C:15]([CH3:21])[N:16]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][Br:23])[CH:8]([CH3:9])[CH3:10])[CH3:4]

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 113249061,1-DibromododecaneHCID 591703963-Methyl-2-(2-methyl-1H-indol-4-yloxy)-butyric acid ethyl ester

Produkt 1

HCID 685477452-[1-(12-Bromo-dodecyl)-2-methyl-1H-indol-4-yloxy]-3-methylbutyric acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of NaH (60% in mineral oil, 0.42 g, 10 mmole) in anhydrous DMF (20 mL), 3-methyl-2-(2-methyl-1H-indol-4-yloxy)-butyric acid ethyl ester (2) (1.88 g, 7.0 mmole) and dibromododecane (2.30 g, 7.0 mmole) were added. The mixture was stirred at room temperature for 18 h. The reaction was diluted with ethyl acetate (50 mL) and washed with water (3×30 mL). The organic layer was separated, dried over sodium sulphate and concentrated. The residue was purified by column chromatography (10:1 Hex:EtOAc) to afford intermediate (3) Yield: intermediate (3) 1.32 g, 35%, by-product (4) 1.56 g, 31%.

Aufarbeitung

  1. additionwere added
  2. washwashed with water (3×30 mL)
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (10:1 Hex:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b67f5df1629e4f6887454f4c59b9e5e0
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07666898B2

Verknüpfte Notizen

Wird geladen…