Ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

Ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate from ethyl 5-Boc-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate: to a 100 mL round-bottom flask containing ethyl 5-Boc-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (1 g. 3.21 mmol) in a 100 mL round-bottomed flask was added to dichloromethane (16 mL) followed by slow addition of trifluoroacetic acid (1.48 mL, 19.3 mmol). The reaction mixture was stirred at room temperature for 60 minutes. After the reaction was completed, saturated aqueous sodium bicarbonate (10 mL) and dichloromethane (10 mL) were added to the mixture. After separating the organic layer, the aqueous phase was extracted twice with dichloromethane (20 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the oily product ethyl 4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate (0.547 g, 81% yield).LCMS(FA)ES+: m/z 212.

References

[1] Patent: WO2010/151317, 2010, A1. Location in patent: Page/Page column 108
[2] Journal of Medicinal Chemistry, 2013, vol. 56, # 18, p. 7201 - 7211
[3] MedChemComm, 2016, vol. 7, # 5, p. 960 - 965
[4] Patent: WO2012/117421, 2012, A1. Location in patent: Page/Page column 40
[5] Patent: US2010/99664, 2010, A1. Location in patent: Page/Page column 32