2-Methylimidazo[1,2-a]pyridine-3-carboxylic acid

Chemical Properties

Pink solid

Synthesis

To a stirred ethyl 2-methylimidazo[1,2-a]pyridine-3-carboxylate (2.00 g) solution of ethanol/water (1:1, 30 mL) was added lithium hydroxide (4.00 g) and the reaction was stirred for 4 hours at room temperature. Upon completion of the reaction, the reaction mixture was concentrated to half of the original volume, followed by the slow addition of 6N hydrochloric acid at 0 °C and adjusting the pH to 6. The precipitated solid was collected by filtration and dried in a vacuum oven to afford 2-methylimidazo[1,2-a]pyridine-3-carboxylic acid (1.53 g, 88% yield) as an off-white solid.ESI-MS analysis showed the molecular ion peaks as 177 [M + H]+.

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 17, p. 7525 - 7545
[2] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 15, p. 4223 - 4232
[3] Farmaco, Edizione Scientifica, 1982, vol. 37, # 1, p. 22 - 35
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 5, p. 1870 - 1873
[5] Journal of Medicinal Chemistry, 2014, vol. 57, # 12, p. 5293 - 5305