Potassium Iodide → 2-Amino-5-bromo-3-iodopyridine

Temperatur

100 °C

A stirred solution of 5-bromo-pyridin-2-ylamine (50 g, 289 mmol) in 2M sulfuric acid (500 mL) was treated portionwise with potassium iodate (30.8 g, 144 mmol) and the mixture heated to 100° C. A solution of potassium iodide (26.5 g, 160 mmol) in water (50 mL) was added dropwise over ca. 1 hour. The mixture was allowed to stir for a further 30 minutes then cooled to ambient temperature. The pH of the aqueous phase was adjusted to 8-9 and the mixture extracted with ethyl acetate (×3). The combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine, dried (Na2SO4) and evaporated to afford the title compound as a brown solid (77.4 g, 90%). 1H NMR (300 MHz, CDCl3): 8.06 (d, J=2.2 Hz, 1H), 7.96 (d, J=2.2 Hz, 1H), 4.96 (s, 2H).

1. temperaturethen cooled to ambient temperature
2. extractionthe mixture extracted with ethyl acetate (×3)
3. washThe combined organic layer was washed with aqueous sodium thiosulfate solution, water and brine
4. dry with materialdried (Na2SO4)
5. customevaporated

ORD-Eintrag

ord-4568b1b4cc8942c8a9b06a4d9f8ea174

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09440976B2