Sodium ethoxide → 4-Azaindole

HRID 2080015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2080015
C(OC(=O)[NH:5][C:6]1[C:7]([C:12]#[C:13][Si](C)(C)C)=[N:8][CH:9]=[CH:10][CH:11]=1)C.[O-]CC.[Na+]>C(O)C.[Cl-].[Na+].O>[NH:5]1[C:6]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[CH:12]=[CH:13]1

Komponenten

5

Edukt 2

HCID 2723922Sodium ethoxideHCID 58875356(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester

Produkt 1

HCID 92264-AzaindoleAusbeute 63,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

(2-Trimethylsilanylethynyl-pyridin-3-yl)carbamic acid ethyl ester described in Preparation Example S-3 (0.42 g, 1.6 mmol) was dissolved in ethanol (8 mL), sodium ethoxide (204 mg, 3 mmol) was added thereto, followed by stirring for 1 hour under reflux. After the reaction was completed, the reaction mixture was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then evaporated, the resulting solid was washed with solvent (diethylether:hexane=1:2), and the title compound (0.12 g, 1 mmol, 63.5%) was obtained.

Aufarbeitung

  1. temperatureunder reflux
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. washthe resulting solid was washed with solvent (diethylether:hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-216d4aea7c184db1a07535b90590f960
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07932272B2

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