Extracurricular laboratory: Synthetic route of 2-Chloro-5-iodopyridine

According to the analysis of related databases, 69045-79-0, the application of this compound in the production field has become more and more popular.

Electric Literature of 69045-79-0, 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 69045-79-0, name is 2-Chloro-5-iodopyridine. This compound has unique chemical properties. The synthetic route is as follows.

To a solution of (S)-1-(phenyl-3-boronic acid)-ethyl]-carbamic acid tert-butyl ester (1.29 g, 4.86 mmol) and 2-chloro-5-Iodo-pyridine (1.4 g, 11.4 mmol) in ethyleneglycoldimethylether (25 mL) in a sealed tube were added cesium carbonate (4.75 g, 14.6 mmol) and water (5 mL). Argon was bubbled in to the above mixture for 10 min, and Pd(PPh3)4 (280 mg, 0.24 mmol) was added. The reaction mixture was stirred at 100 C. for 18 hand then cooled down to room temperature. Ethyl acetate (100 mL) was added, the resulting solution was washed with NH4Cl (sat.) (2¡Á100 mL), and the organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the crude product was diluted in CH2Cl2 (30 mL) and trifluoroacetic acid (10 mL). The reaction mixture was agitated for 1 h and concentrated in vacuo. The residue was purified by solid phase extraction (SCX cartridge, silca gel benzene sulfonic acid linked) to give the title product (785 mg, 69%) as yellow oil. [0147] 1H NMR (DMSO d6, 400 MHz): delta 1.28 (d, 3 H, J=6.8 Hz), 4.04 (q, 1 H, J=6.8 Hz), 7.4-7.45 (m, 2H), 7.5-7.55 (m, 1H), 7.61 (d, 1H J =7.8 Hz,), 7.72 (s, 1H), 8.15 (dd, 1H, J=8.3, 2.5 Hz,), 8.73 (d, 1H, J=3.3 Hz).

According to the analysis of related databases, 69045-79-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Yong-Jin; Sun, Li-Qiang; L’Heureux, Alexandre; US2004/110754; (2004); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem