(1-Bromoethyl)benzene → HCID 89740220, Verbindung

HRID 1526950

Reaktionsgleichung

Reaktionsgleichung von HRID 1526950
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].Br[CH:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH3:20]>CN(C)C=O>[CH3:1][C:2]1[N:3]([CH:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[C:4]2[C:9]([C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

5

Edukt 3

HCID 11454(1-Bromoethyl)benzeneHCID 24758Sodium hydrideHCID 4072358ethyl 2-methyl-1H-indole-3-carboxylate

Produkt 1

HCID 89740220HCID 89740220, VerbindungAusbeute 56,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-methyl-1H-indole-3-carboxylate (400 mg, 1.97 mmol) and sodium hydride (47 mg, 2.0 mmol) in N,N-dimethylformamide (5.0 mL) was stirred at room temperature for 0.5 hours, and then (1-bromoethyl)benzene (361 mg, 2.0 mmol) was added. The mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. Organic layers were combined and concentrated to give a residue. The residue was purified by chromatography (petroleum ether/ethyl acetate=5:1) to give ethyl 2-methyl-1-(1-phenylethyl)-1H-indole-3-carboxylate (340 mg, 56%). LRMS (M+H+) m/z: calcd 307.16. found 307.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 3 hours
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with ethyl acetate
  4. concentrationconcentrated
  5. customto give a residue
  6. customThe residue was purified by chromatography (petroleum ether/ethyl acetate=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-5ea87d184e444d8c9be42214c9bb7d18
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085583B2

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