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

HRID 1529481Notes

Reaction equation

HRID 1529481 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-bebb88c4748d48f6a83f58658fc93112
Source dataset
uspto-grants-2015_07
Patent number
US09090625B2

Reaction notes

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