4-methyl-6H,7H-thieno[3,2-c]pyridine → 4-Methylthieno[3,2-c]pyridine

HRID 1904762Notes

Reaction equation

HRID 1904762 reaction equation
[CH3:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH2:5][CH2:4][N:3]=1>[C].[Pd].C1(C)C(C)=CC=CC=1>[CH3:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 218211774-methyl-6H,7H-thieno[3,2-c]pyridine

Product 1

HCID 2789014-Methylthieno[3,2-c]pyridine

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 7237O-XyleneSolvent

Procedure

To 4.43 g (0.0293 mol) of 4-methyl-6, 7-dihydrothieno[3, 2-c]pyridine (g-1) were added 244 ml of dry xylene and 3.42 g of 10% palladium carbon, and the mixture was refluxed for 34 hr. After being cooled down to room temperature, the solution was filtered. The filtrate was concentrated under reduced pressure and subjected to silica gel column chromatography, eluting with AcOEt - MeOH, whereby 1.47 g (Yield : 33.6%) of the objective product, 4-methylthieno[3, 2-c]pyridine (j-1) was obtained as brown liquid.

Workup

  1. temperaturethe mixture was refluxed for 34 hr
  2. filtrationthe solution was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. washeluting with AcOEt - MeOH, whereby 1.47 g (Yield : 33.6%) of the objective product

Sources & evidence

ORD record
ord-f18bb4609c734b13900ffef86428e734
Source dataset
uspto-grants-1989_06
Patent number
US04839365

Reaction notes

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