Methyl iodide → 2-Methylsulfanylthieno[2,3-b]pyridine-3-carboxylic Acid Ethyl Ester

HRID 2061456

Reaktionsgleichung

Reaktionsgleichung von HRID 2061456
Cl[C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:14](=[S:16])=[S:15].[H-].[Na+].[CH3:19]I>CS(C)=O>[CH2:12]([O:11][C:9]([C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[S:15][C:14]=1[S:16][CH3:19])=[O:10])[CH3:13]

Komponenten

6

Edukt 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 24758Sodium hydrideHCID 15326671Ethyl 2-(2-chloropyridin-3-yl)acetate

Produkt 1

HCID 153266732-Methylsulfanylthieno[2,3-b]pyridine-3-carboxylic Acid Ethyl EsterAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of ethyl (2-chloropyridin-3-yl)acetate (D. H. Bremner et al., Synthesis, 1997, 949) (8.0 g, 40.0 mmol) and carbon disulfide (3.18 g, 42.0 mmol) in DMSO (100 mL) was added sodium hydride portionwise (2.4 g, 60.0 mmol). After 60 minutes stirring at room temperature the mixture was heated at 80° C. for 2 hours. After this time the reaction mixture was allowed to cool to room temperature and methyl iodide (7.6 g, 54.0 mmol) added. After 18 hours ice (50 mL) was added and a yellow precipitate formed which was isolated via filtration to give the title compound as a grey solid (7.95 g, 78%). δH (DMSO-d6) 8.60 (1H, dd, J 1.6, 8.2 Hz), 8.46, (1H, dd, J 1.6, 4.6 Hz), 7.35 (1H, dd, J 4.6, 8.2 Hz), 4.48 (2H, q, J 7.1 Hz), 2.71, (3H, s), 1.49 (3H, t, J 7.1 Hz).

Aufarbeitung

  1. temperaturewas heated at 80° C. for 2 hours
  2. temperatureto cool to room temperature
  3. customa yellow precipitate formed which
  4. customwas isolated via filtration

Quellen und Nachweise

ORD-Eintrag
ord-dfc556b094de4f919023b98aab2e9b04
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08283359B2

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