104830-06-0

Light yellow Needles

2-Amino-3-iodopyridine (3-Iodopyridin-2-amine) can be coupled with formyl derivatives under a copper-catalyzed indole synthesis method, and then constructed azide analogs through copper-mediated conjugated adducts things. The nucleophilicity of 2-Amino-3-iodopyridine is lower than that of the corresponding aniline used in the synthesis of indole, a potential obstacle for future synthesis[1].

General procedure for the synthesis of 2-amino-3-iodopyridine from N-(3-iodopyridin-2-yl)palmitamide: N-(3-iodopyridin-2-yl)neopentanamide (13.80 g, 45.36 mmol) was dissolved in 24 wt% sulfuric acid solution (394 mL), and the reaction mixture was stirred for 60 min under reflux conditions. After completion of the reaction, it was cooled to room temperature and neutralized with 4N sodium hydroxide solution and solid sodium bicarbonate. The aqueous phase was extracted with dichloromethane (3 x 200 mL), the organic phases were combined and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporator to give 3-iodopyridin-2-amine (9.70 g, 97% yield) as a cream colored solid.

[1] Patent: US2009/156593, 2009, A1. Location in patent: Page/Page column 17
[2] Patent: US2006/183758, 2006, A1. Location in patent: Page/Page column 8
[3] Patent: US2009/82403, 2009, A1. Location in patent: Page/Page column 51
[4] Patent: US2007/105904, 2007, A1. Location in patent: Page/Page column 53
[5] Patent: US2010/331282, 2010, A1. Location in patent: Page/Page column 10