Cesium carbonate → Methyl 4-chlorothieno[2,3-c]pyridine-2-carboxylate

HRID 2075331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2075331
Cl[C:2]1[CH:9]=[N:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.C([O-])([O-])=O.[Cs+].[Cs+].[SH:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>CN(C=O)C>[Cl:10][C:6]1[CH:7]=[N:8][CH:9]=[C:2]2[S:17][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:3]=12

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 16907Methyl ThioglycolateHCID 27629883,5-Dichloro-4-pyridinecarboxaldehyde

Produkt 1

HCID 18516294Methyl 4-chlorothieno[2,3-c]pyridine-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3,5-Dichloroisonicotinaldehyde (20.39 g, 115.8 mmol) obtained from Aldrich was dissolved in 250 mL DMF. To this solution was added Cs2CO3 (12.9 g, 121.59 mmol) and then methyl 2-mercaptoacetate (56.6 g, 173.7 mmol). The mixture was stirred at room temperature for 3 hours. After removing 200 mL DMF under a reduced pressure, the remaining residue was mixed with 100 mL water. After filtration, the filter cake was washed thoroughly with water and air dried. An off-white solid was obtained as the pure product (23.15 g, y=88%). LCMS (API-ES) m/z (%): 228.2 (100%, M++H); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.96 (s, 3H) 8.12 (s, 1H) 8.64 (s, 1H) 9.36 (s, 1H).

Aufarbeitung

  1. customAfter removing 200 mL DMF under a reduced pressure
  2. additionthe remaining residue was mixed with 100 mL water
  3. filtrationAfter filtration
  4. washthe filter cake was washed thoroughly with water and air
  5. customdried
  6. customAn off-white solid was obtained as the pure product (23.15 g, y=88%)

Quellen und Nachweise

ORD-Eintrag
ord-14d89d8addaf429cbb13a66aa11697cb
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07919504B2

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