Dimethyl Sulfoxide → 2-Amino-5-fluoro-3-iodopyridine

To a mixture of 2-amino-5-fluoropryidine (2.0 g, 17.8 mmol) and dimethyl sulfoxide (50 mL) was added N-iodosuccinimide (4.8 g, 21.4 mmol), which was stirred for 1 hour at room temperature. A suitable amount of acetic acid was added to this mixture, which was stirred for 1 hour at the same temperature, and then stirred for another 3 hours at 55° C. This reaction mixture was cooled to room temperature, after which a saturated sodium hydrogencarbonate aqueous solution was added, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue thus obtained was purified by NH silica gel column chromatography (ethyl acetate) to obtain the title compound (751 mg, 18%).

1. stirringwas stirred for 1 hour at the same temperature
2. stirringstirred for another 3 hours at 55° C
3. temperatureThis reaction mixture was cooled to room temperature
4. extractionthe mixture was extracted with ethyl acetate
5. customThe organic layer was separated
6. washwashed with water and saturated aqueous sodium chloride
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under a reduced pressure
10. customthe residue thus obtained
11. customwas purified by NH silica gel column chromatography (ethyl acetate)

ORD-Eintrag

ord-004c2271435d4025ac26d2a86bf01c27

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08841327B2