5-Iodo-6-Methoxy-3-nitro-pyridin-2-ylaMine synthesis

Yield:868539-54-2 153 g

Reaction Conditions:

with N-iodo-succinimide;acetic acid at 20 - 27; for 18 h;

Steps:

1 Intermediate 70 5) MeS0₂Na, Cul, 2-picolinic acid Intermediate 71

Step 1) NIS (199 g, 0.88 mol) was added to a suspension of 6-methoxy-3- nitropyridin-2-amine (Intermediate 70, 100 g, 0.59 mol) in acetic acid (1.9 L), the reaction mixture was stirred at rt for 18 h, concentrated in vacuo and partitioned between aqueous sodium hydroxide (1M, 2 L) and EtOAc (2.5 L). The phases were separated and the organic layer was washed with saturated aqueous NaHC0₃ (1.5 L), and brine (1 L), dried (Na₂S0₄), and concentrated in vacuo. The residue was triturated with heptane (1.5 L) and dried in vacuo to yield 5-iodo-6-methoxy-3-nitropyridin-2- amine (153 g, 0.52 mol) as a yellow solid. (0447) LCMS (Method 8): m/z 293.9 (ES-), at 2.11 min. (0448) 1H NMR: (300 MHz, DMSO-i) δ: ppm 3.89 (s, 3H), 8.19 (br s, 2H), 8.52 (s, 1H).

References:

WO2019/86902,2019,A1 Location in patent:Page/Page column 50