Methanol → HCID 71074609, Verbindung

HRID 1851890Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1851890
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Br[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=1.[H-].[Na+].CO>CN(C=O)C>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:1]2[C:9]3[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)=[CH:17][CH:18]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 2737635methyl 1H-indole-5-carboxylate

Produkt 1

HCID 71074609HCID 71074609, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of methyl 1H-indole-5-carboxylate (1.09 g, 6.2 mmol, 1 equiv) and 1-(bromomethyl)-4-bromobenzene (1.70 g, 6.82 mmol, 1.1 equiv) in anhydrous DMF (30 mL) under argon atmosphere was added sodium hydride (500 mg, 12.4 mmol, 2 equiv) in small portions. The mixture was stirred 2 h at room temperature. The reaction mixture was then neutralized by addition of methanol and concentrated in vacuo. The residue was dissolved in AcOEt, washed with brine and dried over MgSO4. The crude was purified by flash chromatography (Hexane/AcOEt 7.5/2.5) to afford the title compound as a white powder (1.09 g, 3.2 mmol, 52%). ESI-MS (m/z): 344/346 [M+H]+.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude was purified by flash chromatography (Hexane/AcOEt 7.5/2.5)

Quellen und Nachweise

ORD-Eintrag
ord-4d1788964f6b4b03baaeed9e21b9a512
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957093B2

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