imidazo[1,2-a]pyridine-6-carboxylic acid

Uses

Imidazo[1,2-a]pyridine-6-carboxylic acid is a brown solid that should be stored sealed at room temperature and away from light. It is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

Step 2. Imidazo[1,2-a]pyridine-6-carboxylic acid hydrochloride (170 g) was dissolved in water (600 mL) and heated until completely dissolved to form a clarified solution. Subsequently, the pH was adjusted to 5-6 by slowly adding 2 M NaOH aqueous solution. the reaction mixture was cooled to 0 °C in an ice-water bath. The precipitate precipitated was collected by vacuum filtration, washed with ethanol and dried under vacuum to afford the target product imidazo[1,2-a]pyridine-6-carboxylic acid (107.2 g, 77% yield) as a light yellow powder. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6) and mass spectrometry (ESI+): 1H NMR δ 13.76-12.82 (br, 1H), 9.28 (s, 1H), 8.10 (s, 1H), 7.68 (s, 1H), 7.64-7.56 (m, 2H); MS (ESI+) m/z: 163 [M + H]+.

References

[1] Patent: WO2013/127266, 2013, A1. Location in patent: Page/Page column 130
[2] Patent: WO2013/127267, 2013, A1. Location in patent: Page/Page column 81; 82
[3] Patent: WO2013/127268, 2013, A1. Location in patent: Page/Page column 59; 60
[4] Patent: WO2013/130943, 2013, A1. Location in patent: Paragraph 0181