4-Methyl-2-phenyl-1,3-thiazole-5-carboxylic acid

Chemical Properties

White solid

Uses

4-Methyl-2-phenyl-1,3-thiazole-5-carboxylic Acid is a useful reagent in Pd-catalyzed decarboxylative C-H cross-coupling of oxazoles and thiazoles.

Synthesis

General method: 2N aqueous sodium hydroxide solution was slowly added to a methanol solution containing ethyl 4-methyl-2-phenyl-1,3-thiazole-5-carboxylate (1 eq.) at room temperature. The reaction mixture was stirred continuously for 4 hours at room temperature. After completion of the reaction, the methanol solvent was removed by rotary evaporator. Subsequently, the pH of the reaction mixture was adjusted to 5-6 with 1N hydrochloric acid solution.The precipitated white solid was collected by filtration and processed by drying to finally give 4-methyl-2-phenylthiazole-5-carboxylic acid (1a-i).

References

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 685 - 695
[2] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 96 - 107
[3] Justus Liebigs Annalen der Chemie, 1974, p. 1195 - 1205
[4] Heterocycles, 2014, vol. 89, # 2, p. 453 - 464
[5] Molecules, 2014, vol. 19, # 7, p. 9240 - 9256