Water → Methyl thieno[3,2-c]pyridine-2-carboxylate

HRID 1890513Notes

Reaction equation

HRID 1890513 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.O.C([O-])([O-])=O.[K+].[K+].[C:17]([O:21][CH3:22])(=[O:20])[CH2:18][SH:19]>CN(C=O)C>[S:19]1[C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[CH:8]=[C:18]1[C:17]([O:21][CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 140466744-Chloropyridine-3-carbaldehyde

Product 1

HCID 22047666Methyl thieno[3,2-c]pyridine-2-carboxylateYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-chloropyridine-3-carboxaldehyde (D-1) (1.4 g, 10 mmol) dissolved in DMF (10 mL) and water (1 mL) were added K2CO3 (1.66 g, 12 mmol) and methyl thioglycolate (1.07 mL, 12 mmol) portion-wise. The reaction mixture was stirred at 45° C. overnight and then quenched with cold water. The flask was placed on ice to enhance precipitation. The precipitate was collected by filtration and air-dried to afford the title compound (1.23 g). MS (m/z): 194 (M+1)+.

Workup

  1. customquenched with cold water
  2. customprecipitation
  3. filtrationThe precipitate was collected by filtration
  4. customair-dried

Sources & evidence

ORD record
ord-6f2ead3612fa4c24bbade45f3b951365
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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