7-Chlorothieno[3,2-b]pyridine → Thienopyridine

HRID 2173028Notes

Reaction equation

HRID 2173028 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12>C(O)(=O)C.[Zn]>[S:10]1[C:3]2[C:4](=[N:5][CH:6]=[CH:7][CH:2]=2)[CH:8]=[CH:9]1

Participants

4

Reactant 1

HCID 112752517-Chlorothieno[3,2-b]pyridine

Product 1

HCID 12210218Thienopyridine

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 7-chlorothieno[3,2-b]pyridine (500 mg, 2.95 mmol) and zinc (193 mg, 2.95 mmol) in acetic acid (5 mL) was stirred at room temperature for 3 days, followed by stirring at 50° C. for 5 hours. The solvent was removed in vacuo and the residue was dissolved in DCM (200 mL) and extracted with 1N NaOH (500 mL). The aqueous layer was washed again with DCM (2×200 mL). The organic layers were combined, dried over Na2SO4, and the solvent was removed in vacuo to yield the title compound as a yellow oil, which was used without further purification. ESI-MS m/z [M+H]+ calc'd for C7H5NS, 136. found, 136.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in DCM (200 mL)
  3. extractionextracted with 1N NaOH (500 mL)
  4. washThe aqueous layer was washed again with DCM (2×200 mL)
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-86ad34e6e52c496790c3b2e5be429d45
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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