Iodine → 3-fluoro-4-iodopyridin-2-amine

Temperature

-78 °C

A solution of 2-amino-3-fluoropyridine (1.0 g, 8.9 mmol) in anhydrous THF (40 ml) was treated dropwise at −78° C. with n-butyllithium (1.6 M in hexanes, 13.9 ml, 22.3 mmol). Following the addition, the mixture was stirred at −78° C. for 1 h, then a solution of iodine (10.2 g, 40.1 mmol) in THF (20 ml) was added. The mixture was extracted with ethyl acetate, and the organic extracts were washed with sodium thiosulfate, sodium bicarbonate and brine. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by silica gel chromatography (8:1 to 2:1 hexanes/ethyl acetate eluant) to provide the title compound. MS m/z 238.9 (M+1).

1. additionthe addition
2. extractionThe mixture was extracted with ethyl acetate
3. washthe organic extracts were washed with sodium thiosulfate, sodium bicarbonate and brine
4. dry with materialThe organic phase was dried over sodium sulfate
5. concentrationconcentrated
6. customThe crude product was purified by silica gel chromatography (8:1 to 2:1 hexanes/ethyl acetate eluant)

ORD record

ord-46aba7536a83480da299e4d9b3aa45dd

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501758B2