Ethanol → 3-Bromo-2-ethoxy-4-methylpyridine

3-bromo-2-chloro-4-methylpyridine obtained in Preparation Example 37(1) (1 g) was added to a mixed solvent of ethanol (2 mL) and DMF (5.6 mL). Sodium hydride (60% oil dispersion, 58 mg) was added to the solution, and the mixture was stirred at 100° C. for five hours. The reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (40% solution in n-heptane, 250 mg).

1. customThe reaction mixture was partitioned
2. additionby adding ethyl acetate and water
3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
4. customThe desiccant was removed by filtration
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

ORD record

ord-b8b20576f2d14896abfeed66049626ad

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08563565B2