p-Toluenesulfonic acid → HCID 69590164, compound

HRID 1822750Notes

Reaction equation

HRID 1822750 reaction equation
[C:1]1([CH:7]2[S:15][C:14]3[C:9]([N:10](Cl)[CH:11]=[CH:12][CH:13]=3)=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C-]#N.[K+].[OH-:31].[Na+].CN([CH:36]=[O:37])C>C(O)C.O>[C:1]1([CH:7]2[S:15][C:14]3[C:9]([N:10]([C:36]([OH:37])=[O:31])[CH:11]=[CH:12][CH:13]=3)=[CH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 6228DimethylformamideHCID 9032Potassium CyanideHCID 14798Sodium HydroxideHCID 22170175HCID 22170175, compound2×

Product 1

HCID 69590164HCID 69590164, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

Prepare 2-phenylthieno[3,2-b]pyridin-4-yl chloride by the method described in PCT application WO 9943682. A mixture containing 400 mg of 2-phenylthieno[3,2-b]pyridin-4-yl chloride, 400 mg of p-toluenesulfonic acid and 200 mg of potassium cyanide in anhydrous DMF is heated at 160° C. in an oil bath for 16 h under nitrogen. The mixture is cooled to ambient temperature, poured into a mixture of ice and water. The resulting mixture is extracted with ethyl acetate and the ethyl acetate layer is washed with water followed by brine. The ethyl acetate solution is dried over sodium sulfate, filtered and evaporated at reduced pressure to obtain a tan-colored residue. This material is dissolved in 10 ml of ethanol, treated with 1 g of sodium hydroxide and heated at reflux for 2 h. The ethanol solution is evaporated and the resulting residue is dissolved in water. The pH of this solution is adjusted to slightly acidic by addition of 1 N HCl to yield 2-phenylthieno[3,2-b]pyridin-4-yl carboxylic acid as a red-orange solid. After drying in vacu this material is pure according to proton NMR and LC/MS.

Workup

  1. temperatureThe mixture is cooled to ambient temperature
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. washthe ethyl acetate layer is washed with water
  4. dry with materialThe ethyl acetate solution is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated at reduced pressure
  7. customto obtain a tan-colored residue
  8. temperatureheated
  9. temperatureat reflux for 2 h
  10. customThe ethanol solution is evaporated
  11. dissolutionthe resulting residue is dissolved in water
  12. additionslightly acidic by addition of 1 N HCl

Sources & evidence

ORD record
ord-78e09057cf5d444d8c39827ac7a243bd
Source dataset
uspto-grants-2006_05
Patent number
US07037922B1

Reaction notes

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