Isopropyl iodide → 3-Bromo-6-isopropyloxy-2,4-dimethylpyridine

KTB (222 mg) was added to a suspension of 5-bromo-4,6-dimethylpyridin-2-ol obtained in Preparation Example 23(1) (400 mg) in DME (2 mL), and the mixture was stirred at room temperature for 30 minutes. Potassium carbonate (192 mg) and 2-iodopropane (572 mg) were added to the reaction mixture. The mixture was heated under reflux overnight. The reaction mixture was cooled to mom temperature, and the insoluble matter was removed by filtration and washed with DME. The filtrate was concentrated under reduced pressure. Chloroform was added to the residue. The solution was washed with a 0.1 N aqueous hydrochloric acid solution. The organic layer was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%) to give the title compound (133.9 mg).

1. temperatureThe mixture was heated
2. temperatureunder reflux overnight
3. temperatureThe reaction mixture was cooled to mom temperature
4. customthe insoluble matter was removed by filtration
5. washwashed with DME
6. concentrationThe filtrate was concentrated under reduced pressure
7. additionChloroform was added to the residue
8. washThe solution was washed with a 0.1 N aqueous hydrochloric acid solution
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under reduced pressure
12. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 10% to 50%)

ORD record

ord-b5fde50b9a0e443ebc990ebcb2c2f3c2

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563565B2