Methanol → methyl 4H,5H,6H,7H-thieno[3,2-c]pyridine-2-carboxylate

HRID 2093090Notes

Reaction equation

HRID 2093090 reaction equation
[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([OH:12])=[O:11].S(Cl)(Cl)=O.[CH3:17]O>>[S:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[CH:3]=[C:2]1[C:10]([O:12][CH3:17])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 142549064,5,6,7-Tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid

Product 1

HCID 18697868methyl 4H,5H,6H,7H-thieno[3,2-c]pyridine-2-carboxylate

Procedure

To a solution of 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid (1 eq) obtained in step IV in methanol was added thionyl chloride (1.5 eq) at 0° C., and the reaction was refluxed for 3.0 h Reaction mixture was concentrated and neutralized to afforded the methyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate.

Workup

  1. temperaturethe reaction was refluxed for 3.0 h
  2. customReaction mixture
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-68e2ae476958492bb1f66b27d5b50ece
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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