Potassium hydroxy sulfite → 5-chloro-6-[(1S)-2,2,2-trifluoro-1-methylethoxy]pyridin-3-ol

Temperature

0 °C

To a solution of 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-[(1S)-2,2,2-trifluoro-1-methylethoxy]pyridine (Preparation 232, 130 mg, 0.37 mmol) in acetone (1 mL) was added an aqueous solution of Oxone® (1 mL, 287 mg, 0.44 mmol) dropwise with stirring at 0° C. for 15 minutes. The reaction mixture was diluted with water and extracted with DCM (3×5 mL). The mixture was filtered through a phase separation cartridge, the organic phase was washed with brine (3 mL) and filtered through another phase separation cartridge. The filtrate was dried by N2 blowing to give a crude product that was purified by silica gel column chromatography eluting with 0-30% EtOAc in heptane to give the title compound (62 mg, 69%) as colourless oil.

1. extractionextracted with DCM (3×5 mL)
2. filtrationThe mixture was filtered through a phase separation cartridge
3. washthe organic phase was washed with brine (3 mL)
4. filtrationfiltered through another phase separation cartridge
5. dry with materialThe filtrate was dried by N2 blowing
6. customto give a crude product that
7. customwas purified by silica gel column chromatography
8. washeluting with 0-30% EtOAc in heptane

ORD record

ord-21c1fcf8c73e458c9f4e030cbf2e8ecf

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2