Dimethylformamide → 5-Bromo-2-iodo-3-methoxypyridine

Temperature

0 °C

To a stirred solution of 5-bromo-2-iodopyridin-3-ol (2.17 g, 7.2 mmol) in DMF (10.00 mL, 129 mmol) was added NaH (0.32 g, 8.0 mmol) at 0° C. The resulting mixture was stirred at 0° C. and MeI was added at 0° C. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with NH4Cl(aq) and water (10 mL each) at 0° C., and diluted with EtOAc (15 mL). The separated aqueous layer was extracted with EtOAc (2×15 mL) and the combined organic layers were washed with water and saturated sodium chloride, dried over Na2SO4, and concentrated to give the crude residue which was purified with flash column chromatography ((5%→50% EtOAc in hexane) to obtain 5-bromo-2-iodo-3-methoxypyridine as an off-white solid (1.77 g, 78% yield) m/z (%): 314.2 (100%, M++H).

1. stirringThe resulting mixture was stirred at room temperature for 2 hours
2. extractionThe separated aqueous layer was extracted with EtOAc (2×15 mL)
3. washthe combined organic layers were washed with water and saturated sodium chloride
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customto give the crude residue which
7. customwas purified with flash column chromatography ((5%→50% EtOAc in hexane)

ORD record

ord-403d3c1b33fa4b7f83109855ff811d70

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084479B2