Sodium Azide → Ethyl 3-(azidomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

HRID 23650

Reaktionsgleichung

Reaktionsgleichung von HRID 23650
Br[CH2:2][C:3]1[C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:12])[C:6]=2[S:5][CH:4]=1.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:2][C:3]1[C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11](=[O:12])[C:6]=2[S:5][CH:4]=1)=[N+:20]=[N-:21]

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 22574331Ethyl 3-(bromomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate

Produkt 1

HCID 22574297Ethyl 3-(azidomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylateAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 1.14 g of ethyl 3-(bromomethyl)-4-methyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 19) and 337 mg of sodium azide in 6 mL of DMF is stirred at room temperature for 3 h, then diluted slowly with water to a volume of 50 ml. The resulting solid is filtered, washed well with water, and dried in vacuo to afford 759 mg of the title compound as a cream colored solid. Recrystallization of a sample from acetonitrile gives tan needles.

Aufarbeitung

  1. filtrationThe resulting solid is filtered
  2. washwashed well with water
  3. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f8186607d3cd47e6b57e32d259546a51
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852731B2

Verknüpfte Notizen

Wird geladen…