Sodium Azide → 3-(2-azidoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

HRID 1918626Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1918626
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17].[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]#[N:14])[CH:11]=2)[NH:6][C:5]=1[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17])=[N+:23]=[N-:24]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 668319283-(2-bromoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

Produkt 1

HCID 866638383-(2-azidoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 3-(2-bromoethyl)-2-(triethylsilyl)-1H-indole-5-carbonitrile (0.906 g; 2.49 mmol) and sodium azide (0.486 g; 7.48 mmol) in DMF (7 mL) was stirred at 70° C. for 4 hours and concentrated under reduced pressure. The residue was diluted in ethyl acetate, washed with brine, dried and concentrated under reduced pressure to yield 0.900 g (quantitative) of the title compound as a brown oil.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted in ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f5101ed3b33346a1a3a6376b2cdaf3a0
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618138B2

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