Uses
2-Amino-5-iodopyridine is a compound that can be used in organic synthesis.
Application
2-Amino-5-iodopyridine, also known as 2-amino-5-iodopyridine or 5-iodo-2-aminopyridine, is an important intermediate in organic synthesis. It is mainly used as a pharmaceutical intermediate, and also in the production of dyes, pesticides, and fragrances.
Chemical Properties
Light yellow needles
Synthesis
Example 20: Scheme C10
2-Aminopyridine (II) (1.0 eq, 318 mmol, 30.0 g), periodate dihydrate (0.15 eq, 48 mmol, 10.7 g), and iodine (0.42 eq, 134 mmol, 32.4 g) were dissolved in a mixture of acetic acid (800 mL), water (36 mL), and sulfuric acid (6.2 mL), and heated to react at 80°C for 4 for 4 hours. Upon completion of the reaction, the reaction mixture was poured into 10% Na2S2O3 aqueous solution to quench unreacted iodine and subsequently extracted with ether. The organic phases were combined, washed with 10% NaOH aqueous solution, dried over anhydrous MgSO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (elution gradient: heptane/ethyl acetate 25:75 → pure ethyl acetate) to afford the target compound 2-amino-5-iodopyridine (116) (52.0 g, 74% yield).
1H NMR (δ, CDCl3): 4.51 (2H, s), 6.35 (1H, d, J = 8 Hz), 7.62 (1H, d, J = 8 Hz), 8.21 (1H, s).
References
[1] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 5, p. 2656 - 2663
[2] European Journal of Medicinal Chemistry, 2010, vol. 45, # 3, p. 1211 - 1219
[3] Synthetic Communications, 2010, vol. 40, # 23, p. 3506 - 3513
[4] Synthetic Communications, 2013, vol. 43, # 21, p. 2913 - 2925
[5] Journal of the American Chemical Society, 2003, vol. 125, # 3, p. 616 - 617
