5-Bromoindole-2-carboxylic acid

• Discovery of indole inhibitors of MMP-13 for treatment of arthritic diseases
• Synthesis of indolyl ethanones as indoleamine 2,3-dioxygenase inhibitors
• cis-Diaminocyclohexane derivatives prepared for use as factor Xa inhibitors
• Synthesis of tubulin polymerization inhibitors and cancer cell growth inhibitors
• Preparation of dual PPARγ/δ agonists
• Synthesis of chemical probes to examine the role of hFPRL1 receptor in inflammation

16732-70-0

7254-19-5

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.