7254-19-5

5-Bromoindole-2-carboxylic acid,Reactant involved in studies of biologically active molecules including:Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases1;Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors2 ;cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors3 ;Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors4 ;Preparation of dual PPARγ/δ agonists5;Synthesis of chemical probes to examine the role of hFPRL1 receptor .

The general procedure for the synthesis of 5-bromoindole-2-carboxylic acid from ethyl 5-bromoindole-2-carboxylate was as follows: 134 g of ethyl 5-bromoindole-2-carboxylate was dissolved in a solvent mixture of 31.25 g of 96% methanol and 183 mL of water, and was heated and refluxed for 0.5 h. The reaction was completed with the addition of 10% hydrochloric acid. After completion of the reaction, it was cooled to 40 °C and the pH was adjusted to 3-4 by slowly adding 10% hydrochloric acid solution.Subsequently, the reaction mixture was filtered to give 109.1 g of off-white solid 5-bromoindole-2-carboxylic acid in 91% yield, which was analyzed by high-performance liquid chromatography (HPLC) and showed ≥96% purity.

[1] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7512 - 7527
[2] Advanced Synthesis and Catalysis, 2016, vol. 358, # 24, p. 3938 - 3942
[3] Patent: CN104402795, 2017, B. Location in patent: Paragraph 0050; 0053