Hydrochloric Acid → HCID 18398665, compound

Reaction equation

Cl.[S:2]1[C:10]2[C:5](=[N:6][C:7]([C:11]([OH:13])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[CH3:14]O>>[S:2]1[C:10]2[C:5](=[N:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 12210216Thieno[3,2-b]pyridine-5-carboxylic acid

Product 1

HCID 18398665HCID 18398665, compoundYield 70%

Procedure

To a solution of HCl (10%) in MeOH (10 mL) was added thieno[3,2-b]pyridine-5-carboxylic acid (1.0 g, 5.6 mmol, from Step 2, Example 1) and the mixture heated to reflux for 2 hr. After cooling to r.t., half the solvent was removed by evaporation and the remainder was partitioned between EtOAc and H2O. Solid NaHCO3 was added until the system remained basic. Separation, drying, and evaporation of the organic layer afforded 0.75 g (70%) of methyl thieno[3,2-b]pyridine-5-carboxylate.