N-Iodosuccinimide → 5-Bromo-2-iodopyridin-3-amine

3-Amino-5-bromopyridine (13.8 g, 79.8 mmol) was dissolved in acetic acid (440 mL) and placed under a nitrogen atmosphere. N-Iodosuccinimide (16.15 g, 71.8 mmol) was charged to the reaction which was stirred at room temperature overnight. The reaction was concentrated and the residue partitioned between EtOAc (200 mL) and saturated aqueous sodium hydrogen carbonate (200 mL). The layers were separated and the organic phase was washed with saturated aqueous sodium hydrogen carbonate (200 mL). The aqueous phase was extracted with EtOAc (3×200 mL). The organic extracts were dried over magnesium sulfate, filtered and concentrated. Chromatography (silica; 1.4 Kg packed in 70% DCM:30% heptane, eluting with 70-100% DCM in heptane) gave the title compound (11.5 g). 1H NMR (270 MHz, CDCl3): 7.83 (1H, m), 7.04 (1H, m), 4.33 (2H, br s).

1. concentrationThe reaction was concentrated
2. customthe residue partitioned between EtOAc (200 mL) and saturated aqueous sodium hydrogen carbonate (200 mL)
3. customThe layers were separated
4. washthe organic phase was washed with saturated aqueous sodium hydrogen carbonate (200 mL)
5. extractionThe aqueous phase was extracted with EtOAc (3×200 mL)
6. dry with materialThe organic extracts were dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. washChromatography (silica; 1.4 Kg packed in 70% DCM:30% heptane, eluting with 70-100% DCM in heptane)

ORD record

ord-84d25e357bce45ed81cee2c675f2e8cf

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018214B2