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

Thionyl Chloride → 2-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

HRID 1969528
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1969528
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20](O)[CH2:21][CH:22]=[CH2:23])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].S(Cl)(Cl)=O.C([O-])(O)=O.[Na+].[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)Cl.CCOC(C)=O>[N:34]([CH:20]([C:18]1[N:19]=[C:14]2[CH:13]=[CH:12][N:11]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[C:15]2=[N:16][CH:17]=1)[CH2:21][CH:22]=[CH2:23])=[N+:35]=[N-:36]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 516892Sodium Bicarbonate2×HCID 58557357HCID 58557357, Verbindung

Produkt 1

HCID 585572372-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazineAusbeute 101,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

To a solution of 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)but-3-en-1-ol (0.14 g, 0.41 mmol) in DCM (10 mL) was added thionyl chloride (0.045 mL, 0.61 mmol). The reaction mixture was stirred for about 8 h at ambient temperature and then EtOAc and saturated aqueous NaHCO3 (10 mL each) were added. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concd in vacuo. The crude chloride was dissolved in DMF (10 mL) and sodium azide (0.159 g, 2.45 mmol) was added to the reaction mixture. The reaction mixture was stirred for about 15 h at ambient temperature and then EtOAc and saturated aqueous NaHCO3 (10 mL each) were added to the reaction mixture. The organic layer was separated, concd in vacuo, and purified by chromatography on silica gel eluting with 10-60% EtOAc in heptane to provide 2-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.153 g, 87%) as an oil: LC/MS (Table 1, Method a) Rt=2.84 min; MS m/z: 369 (M+H)+.

Aufarbeitung

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. dissolutionThe crude chloride was dissolved in DMF (10 mL)
  5. stirringThe reaction mixture was stirred for about 15 h at ambient temperature
  6. customThe organic layer was separated
  7. customconcd in vacuo, and purified by chromatography on silica gel eluting with 10-60% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-7f558fc3533640439f601258d14e8038
Quelldatensatz
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08426411B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion