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 ethyl acetate (2×30 mL) and the combined organic extracts washed with brine (30 mL), dried over magnesium sulphate and filtered. The solvent was removed under reduced pressure to give a yellow oil (3.66 g). Purification by flash column chromatography (Biotage™ 50 g silica cartridge) eluting with a gradient of dichloromethane/methanol (100% to 90% to 80%) gave the title compound (1.94 g, 73%) as a white solid.

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 ethyl acetate (2×30 mL)
6. washthe combined organic extracts washed with brine (30 mL)
7. dry with materialdried over magnesium sulphate
8. filtrationfiltered
9. customThe solvent was removed under reduced pressure

ORD record

ord-4d5ca3b822174c7ab604cb2c64106fcb

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102621B2