Potassium Carbonate → Methyl 4-{[(5-chloro-6-isobutoxypyridin-3-yl)oxy]methyl}benzoate

To a solution of methyl 4-(bromomethyl)benzoate (250 mg, 1.09 mmol) in acetone (20 mL) were added potassium carbonate (302 mg, 2.18 mmol) and 5-chloro-6-isobutoxypyridin-3-ol (Preparation 1, 220 mg, 1.09 mmol) and the reaction heated at reflux overnight. The reaction was allowed to cool to room temperature, the solvent removed under reduced pressure and the resulting yellow solid dissolved in ethyl acetate (30 mL). The solution was transferred to a separating funnel containing water (50 mL), the organic layer separated and the aqueous extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with sodium hydroxide (1.0 M aqueous solution, 30 mL), then brine (50 mL), dried over sodium sulphate and filtered to give the title compound as pale yellow solid (369 mg, 97%).

1. temperaturethe reaction heated
2. temperatureat reflux overnight
3. customthe solvent removed under reduced pressure
4. dissolutionthe resulting yellow solid dissolved in ethyl acetate (30 mL)
5. customThe solution was transferred to a separating funnel
6. additioncontaining water (50 mL)
7. customthe organic layer separated
8. extractionthe aqueous extracted with ethyl acetate (2×30 mL)
9. washThe combined organic extracts were washed with sodium hydroxide (1.0 M aqueous solution, 30 mL)
10. dry with materialbrine (50 mL), dried over sodium sulphate
11. filtrationfiltered

ORD record

ord-3f4175e757a24f5dbb6d73862a0ea17f

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102621B2