105752-11-2

3-Amino-4-iodopyridine is a heterocyclic derivative and can be used as a pharmaceutical intermediate.

ChEBI: 3-amino-4-iodopyridine is an aminopyridine that is 3-aminopyridine carrying an additional iodo substituent at postion 4. It has a role as a Saccharomyces cerevisiae metabolite. It is an aminopyridine and an organoiodine compound.

General procedure for the synthesis of 3-amino-4-iodopyridine from N-(4-iodo-3-pyridinyl)-2,2-dimethylpropanamide: N-(4-iodo-3-pyridinyl)-2,2-dimethylpropanamide (20.00 g, 65.76 mmol) was placed in a 2 L round-bottomed flask, and 24% sulfuric acid aqueous solution (640 mL) was added. The mixture was carefully heated to 100 °C and kept for 4 hours. The progress of the reaction was monitored by analytical HPLC. Upon completion of the reaction, the mixture was cooled to room temperature and the pH was slowly adjusted to 7-8 with 4 N NaOH solution (~700 mL).Subsequently, saturated sodium bicarbonate solution was added and extracted with dichloromethane (3 x 500 mL). The organic phases were combined and concentrated to give 3-amino-4-iodopyridine (13.3 g, 92% yield).

[1] Journal of Medicinal Chemistry, 2007, vol. 50, # 26, p. 6519 - 6534
[2] Patent: WO2006/86609, 2006, A2. Location in patent: Page/Page column 154
[3] Patent: EP1595881, 2005, A1. Location in patent: Page/Page column 57
[4] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 1, p. 11 - 16
[5] Tetrahedron Letters, 2004, vol. 45, # 46, p. 8569 - 8573