Analyzing the synthesis route of 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid.

Related Products of 849068-61-7, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 849068-61-7, name is 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid. This compound has unique chemical properties. The synthetic route is as follows.

Example 1; Methyl 5-bromo-l/7-pyrrolo [2,3-/>] pyridine-3-carboxylate; A solution of 5-bromo-l//-pyrrolo[2,3-6]pyridine (0.200 g, 1.01 mmol; described in: Mazeas,D. et al, Heterocycles 1999, 50, 1065-1080) in dichloromethane (12 mL) was added to asuspension of aluminum chloride (0.704 g, 5.28 mmol) in dichloromethane (5 mL) under anatmosphere of nitrogen. The resulting mixture was stirred at room temperature for 40 min togive a brownish solution. Trichloroacetyl chloride (0.56 mL, 5.0 mmol) was added and themixture was stirred at room temperature for 17 h. Methanol (10 mL) was added and thesolvent was evaporated in vacuo. The residue was treated with aqueous potassium hydroxide(3 M, 10 mL) and methanol (5 mL) and heated at 60 C for 1 h and 15 min. The mixture wasallowed to cool to room temperature and the pH was adjusted to 1-2 using aqueoushydrochloric acid (2 M). The aqueous phase was extracted with ethyl acetate, dried oversodium sulfate, and the solvent was evaporated to give a brown residue. Acetyl chloride (10mL) was added dropwise to cooled methanol (0 C, 20 mL). The resulting solution was addedto a solution of the brown residue in methanol (10 mL) at room temperature, and the resultingmixture was heated at reflux for 3 h. The mixture was allowed to cool to room temperatureand the solvent was evaporated to give a yellow solid. The crude product was purified on asilica gel column using a gradient, ethyl acetate/heptane mixture (10, 20, 30,40, 50% ethylacetate), as the eluent to give 0.165 g (64% yield) of the title compound as a pale pink solid:’H NMR (DMSO-d6, 300 MHz) 5 12.80 (br s, 1 H), 8.41 (s, 2 H), 8.30 (d, J= 3.0 Hz, 1 H),3.83 (s, 3 H); 13C NMR (DMSO-d6, 75 MHz) 6 163.9, 147.0, 144.1, 134.5,130.5, 119.6,113.1, 105.0, 51.1; MS (ES) m/z 255 and 257 (M++l).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 849068-61-7, 5-Bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid.

Reference:
Patent; ASTRAZENECA AB; WO2006/1754; (2006); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem