Sodium Azide → 3-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1777583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1777583
Br[CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[NH:6][C:5]=1[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16].[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[C:10]([Cl:13])[CH:11]=2)[NH:6][C:5]=1[Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])=[N+:22]=[N-:23]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 668319713-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 866638403-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The mixture of 3-(2-bromoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine (1.05 g; 2.81 mmol) and sodium azide (0.547 g; 8.43 mmol) in DMF (8 mL) was stirred for 18 hours at 80° C. and was concentrated in vacuo. The residue was partitioned between water and dichloromethane. After separation, the dichloromethane solution was dried over magnesium sulfate and was evaporated to give 0.943 g (100%) of 3-(2-azidoethyl)-5-chloro-2-(triethylsilyl)-1H-pyrrolo[2,3-b]pyridine as a solid.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. customThe residue was partitioned between water and dichloromethane
  3. customAfter separation
  4. dry with materialthe dichloromethane solution was dried over magnesium sulfate
  5. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-c3674a54c9ef402c9859084e7d5c8db2
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266832B2

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