N-Iodosuccinimide → 4-Chloro-5-iodopyridin-2-amine

Temperature

80 °C

4-Chloropyridin-2-amine (0.142 g, 1.10 mmol) and N-iodosuccinimide (0.273 g, 1.22 mmol) were combined in 1.5 mL of acetic acid. The solution was sonicated briefly and then heated to 80° C. After 1 hour the solution was cooled to room temperature and then concentrated under vacuum. After adjusting the pH to ˜ 8/9 with aqueous ammonia, a light brown solid was collected by filtration. The solid was purified on a 12 g Combiflash column eluting with a gradient of DCM to 5% methanol/0.25% NH4OH (˜28% in water)/DCM. The fractions containing the product were combined and concentrated under vacuum to give 4-chloro-5-iodopyridin-2-amine (187 mg, 67%) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.20 (1 H, s), 6.69 (1 H, s), 6.40 (2 H, s); LCMS-ESI (POS), M/Z, M+1: Found 254.9.

1. customThe solution was sonicated briefly
2. temperatureAfter 1 hour the solution was cooled to room temperature
3. concentrationconcentrated under vacuum
4. filtrationa light brown solid was collected by filtration
5. customThe solid was purified on a 12 g Combiflash column
6. washeluting with a gradient of DCM to 5% methanol/0.25% NH4OH (˜28% in water)/DCM
7. additionThe fractions containing the product
8. concentrationconcentrated under vacuum

ORD record

ord-d790b5766a0d4515905ce822406577a5

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841312B2