Peracetic Acid → 5-Chloro-6-isobutoxypyridin-3-OL

Temperature

0 °C

To a suspension of 5-chloro-6-isobutoxypyridin-3-ylboronic acid (3.02 g, 13.1 mmol) in acetic acid/water (1:1, 20 mL) cooled to 0° C. was slowly added peracetic acid (3.9 mL, 20.0 mmol) and the reaction mixture was maintained at 0° C. for 1.5 hours and then at room temperature for 1 hour. Additional peracetic acid (3.9 mL, 20.0 mmol) was added and the reaction stirred at room temperature for 40 minutes after which time the suspension dissolved. The reaction mixture was quenched with sodium thiosulphate solution (15 mL) and stirred for 5 minutes. The mixture was extracted with EtOAc (2×30 mL) and the combined organic extracts washed with brine (30 mL), dried over magnesium sulfate and filtered. The solvent was removed under reduced pressure to afford a yellow oil (3.66 g). The oil was purified by silica gel chromatography (Biotage™ 50 g) eluting with 80 to 100% methanol in DCM to afford the title compound as a white solid (1.94 g, 73%):

1. temperaturethe reaction mixture was maintained at 0° C. for 1.5 hours
2. dissolutiondissolved
3. customThe reaction mixture was quenched with sodium thiosulphate solution (15 mL)
4. stirringstirred for 5 minutes
5. extractionThe mixture was extracted with EtOAc (2×30 mL)
6. washthe combined organic extracts washed with brine (30 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. customThe solvent was removed under reduced pressure

ORD record

ord-a1d289454fd94a05873af92f6b525909

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2