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

HRID 58627Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58627
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=2)[NH:6][C:5]=1[Si:17]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:18][CH3:19].[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C>[N:24]([CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:11]=2)[NH:6][C:5]=1[Si:17]([CH2:22][CH3:23])([CH2:20][CH3:21])[CH2:18][CH3:19])=[N+:25]=[N-:26]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 668317303-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole

Produkt 1

HCID 866638363-(2-azidoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indoleAusbeute 99,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 3-(2-bromoethyl)-2-(triethylsilyl)-5-(trifluoromethyl)-1H-indole (0.448 g; 1.10 mmol) and sodium azide (0.215 g; 3.31 mmol) in DMF (10 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 give 0.402 g (99%) 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-3a07a57a71744cc8bce1fc801b9d0e39
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

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