Isopropanol → 4-Iodo-2-isopropyloxy-3,5-dimethylpyridine

Sodium hydride (60% oil dispersion, 191 mg) was added to a solution of IPA (0.77 mL) in THF (5 mL). After foaming was stopped, a solution of 2-fluoro-4-iodo-3,5-dimethylpyridine obtained in Preparation Example 29 (500 mg) in THF (5 mL) was added to the solution, and the mixture was stirred at mom temperature for two hours. The mixture was stirred at 50° C. for two hours, and the reaction mixture was then cooled to room temperature. The reaction mixture was cooled at 0° C., and MTBE (20 mL) and water (20 mL) were then added. The organic layer was separated. The organic layer was washed with brine. The combined aqueous layers were extracted with MTBE. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to give the title compound (490 mg).

1. additionwas added to the solution
2. stirringThe mixture was stirred at 50° C. for two hours
3. temperatureThe reaction mixture was cooled at 0° C.
4. customThe organic layer was separated
5. washThe organic layer was washed with brine
6. extractionThe combined aqueous layers were extracted with MTBE
7. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-67ac975e7ff948c68a5c94a2516fef3c

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563565B2