Sodium Carbonate → HCID 90389673, compound

Temperature

-20 °C

To a cold (−20° C.), stirred suspension of the 3-iodo-4-methoxypyridin-2-amine (2.5 g, 10 mmol) in HBF4 (70 mL, 470 mmol) was added an aqueous solution of NaNO2 (1.67 M, 6 mL, 10 mmol) over 20 min. The reaction turned green and then brown in color. The mixture was stirred at 0° C. for 3 h. The reaction was then carefully poured into a cold (0° C.) saturated solution of Na2CO3 (50 g) in H2O (100 mL). The layer was then extracted with EtOAc (×3). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under vacuum to leave a residue which was purified by column chromatography on silica gel (elution with 5:1 to 2:1 hexanes:ethyl acetate) to yield 2-fluoro-3-iodo-4-methoxypyridine as a light yellow solid.

1. stirringThe mixture was stirred at 0° C. for 3 h
2. extractionThe layer was then extracted with EtOAc (×3)
3. dry with materialThe combined organic layers were dried over anhydrous MgSO4
4. filtrationfiltered
5. concentrationconcentrated under vacuum
6. customto leave a residue which
7. customwas purified by column chromatography on silica gel (elution with 5:1 to 2:1 hexanes:ethyl acetate)

ORD record

ord-940df2b609564ca49e67ea9a7eb5af63

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09440952B2