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

HRID 1775414Notes

Reaction equation

HRID 1775414 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=O.C([O-])([O-])=O.[K+].[K+].[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18]>CN(C=O)C.O>[CH3:21][O:20][C:16]([C:17]1[S:18][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[CH:8]=1)=[O:19]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 111167404-Bromopyridine-3-carbaldehyde

Product 1

HCID 22047666Methyl thieno[3,2-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 4-bromo-pyridine-3-carbaldehyde (1.50 g, 8.06 mmol) in DMF (10 mL) and water (1 mL) was added K2CO3 (1.34 g, 9.68 mmol) and methyl thioglycolate (0.87 mL, 9.68 mmol). The mixture was heated at 45° C. for 18 hours. The reaction mixture was removed from the heating bath and diluted with water (50 mL). After 1 hour, the fluffy solid that formed was filtered and washed with water. The material thus obtained was dried in a 60° C. vacuum oven to a constant weight of 0.92 g (59%). MS m/z 194 (M+H)+.

Workup

  1. customThe reaction mixture was removed from the heating bath
  2. additiondiluted with water (50 mL)
  3. customthe fluffy solid that formed
  4. filtrationwas filtered
  5. washwashed with water
  6. customThe material thus obtained
  7. customwas dried in a 60° C. vacuum oven to a constant weight of 0.92 g (59%)

Sources & evidence

ORD record
ord-9e733d148eaf4c31bc40cd2601aa768a
Source dataset
uspto-grants-2016_02
Patent number
US09260450B2

Reaction notes

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