StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Azidotrimethylsilane → ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

HRID 455618
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 455618
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].[Br:8][C:9]1[CH:10]=[C:11]2[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(O)[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([I:30])[CH:20]=3)[O:15][C:12]2=[N:13][CH:14]=1>C1(C)C=CC=CC=1>[N:1]([C:22]1([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:11]2[C:12](=[N:13][CH:14]=[C:9]([Br:8])[CH:10]=2)[O:15][C:16]2[C:21]1=[CH:20][C:19]([I:30])=[CH:18][CH:17]=2)=[N+:2]=[N-:3]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 78378AzidotrimethylsilaneHCID 67382689ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

Produkt 1

HCID 86761966ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Azidotrimethylsilane (1.102 ml, 8.32 mmol) was added to a suspension of ethyl 2-(3-bromo-5-hydroxy-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate (2.33 g, 4.75 mmol) in toluene (31.7 ml). The reaction mixture was cooled to 0° C. and (diethyloxonio) trifluoroborate (0.753 ml, 5.94 mmol) was added slowly. The reaction mixture was allowed to warm to RT. After 30 min, the reaction mixture was quenched with MeOH (5 mL) followed by aqueous, saturated NaHCO3 solution (10 mL). The reaction mixture was extracted twice with EtOAc. The combined organic phases were washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford ethyl 2-(5-azido-3-bromo-7-iodo-5H-chromeno[2,3-b]pyridin-5-yl)acetate as a yellow solid.

Aufarbeitung

  1. temperatureto warm to RT
  2. customthe reaction mixture was quenched with MeOH (5 mL)
  3. extractionThe reaction mixture was extracted twice with EtOAc
  4. washThe combined organic phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e2c4ccaaf64b49998a2d6333937c852e
Quelldatensatz
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08497264B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion