Acetonitrile → Methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-C]pyridine-2-carboxylate

HRID 468663Notes

Reaction equation

HRID 468663 reaction equation
[S:1]1[C:5]2=[CH:6][N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]([O:12][CH3:13])=[O:11].[C:14](#N)C>[Pt](=O)=O.CO>[CH3:14][N:7]1[CH2:8][CH2:9][C:4]2[CH:3]=[C:2]([C:10]([O:12][CH3:13])=[O:11])[S:1][C:5]=2[CH2:6]1

Participants

5

Reactant 2

HCID 6342AcetonitrileHCID 20594257Methyl thieno[2,3-c]pyridine-2-carboxylate

Product 1

HCID 58157676Methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-C]pyridine-2-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of methyl thieno[2,3-c]pyridine-2-carboxylate (370 mg, 1.9 mmol) and acetonitrile (7.3 mL) was stirred at 42° C. for 6 h over which time the formation of a precipitate was observed. Upon cooling to room temperature, the solvent was removed in vacuo. To the material thus obtained was added methanol (10 mL) and platinum dioxide (100 mg, 0.4 mmol). The mixture was stirred under a balloon H2 atmosphere pressure for 4 h. The solvent was then removed under reduced pressure and the residue obtained was partitioned between EtOAc and saturated aqueous NaHCO3. Upon separation, the aqueous layer was extracted with EtOAc three additional times. The combined organic phases were further washed with saturated aqueous NaHCO3, water and brine, dried over anhydrous MgSO4 and concentrated to give methyl 6-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine-2-carboxylate (0.4 g, 95%) as an off-white solid. LCMS: (FA) ES+ 212; 1H NMR (CDCl3, 300 MHz) δ7.50 (s, 1 H ), 3.85 (s, 3 H ), 3.64 (m, 2H), 2.73 (m, 4 H ), 2.48 (s, 3 H ).

Workup

  1. customthe solvent was removed in vacuo
  2. customTo the material thus obtained
  3. customThe solvent was then removed under reduced pressure
  4. customthe residue obtained
  5. customwas partitioned between EtOAc and saturated aqueous NaHCO3
  6. customUpon separation
  7. extractionthe aqueous layer was extracted with EtOAc three additional times
  8. washThe combined organic phases were further washed with saturated aqueous NaHCO3, water and brine
  9. dry with materialdried over anhydrous MgSO4
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-71f6b8640dcf433993b23bcf78072d47
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Reaction notes

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