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

HRID 2075331Notes

Reaction equation

HRID 2075331 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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%)

Sources & evidence

ORD record
ord-14d89d8addaf429cbb13a66aa11697cb
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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