Sodium Acetate → 3-Methylthieno[3,2-b]pyridine

HRID 1773507Notes

Reaction equation

HRID 1773507 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:11])=[CH:9][S:10][C:5]2=[C:4](Cl)[CH:3]=1.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[N:7]=[C:6]2[C:8]([CH3:11])=[CH:9][S:10][C:5]2=[CH:4][CH:3]=1.[CH3:11][C:8]1[C:6]2=[N:7][CH:2]=[CH:3][CH:4]=[C:5]2[S:10][CH:9]=1

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 580561725,7-Dichloro-3-methylthieno[3,2-B]pyridine

Product 2

HCID 577526103-Methylthieno[3,2-b]pyridineHCID 580562155-Chloro-3-methylthieno[3,2-B]pyridine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5,7-dichloro-3-methyl-thieno[3,2-b]pyridine (1.2 g), palladium hydroxide on carbon (20%, 600 mg) and sodium acetate (1.0 g) in ethyl acetate (50 mL) was shaken in a Parr apparatus under hydrogen atmosphere (55 PSI) for 62 hours. The resulting mixture was filtered on a CELITE™ pad, the filter cake was washed with dichloromethane and the filtrate was evaporated under reduced pressure. The crude residue was purified by flash chromatography (acetone/hexane) to afford 0.4 g of 5-chloro-3-methyl-thieno[3,2-b]pyridine and 0.2 g of 3-methyl-thieno[3,2-b]pyridine.

Workup

  1. filtrationThe resulting mixture was filtered on a CELITE™ pad
  2. washthe filter cake was washed with dichloromethane
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe crude residue was purified by flash chromatography (acetone/hexane)

Sources & evidence

ORD record
ord-f588e8a3440244648fce5049a4980943
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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