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To a solution of 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-[(1R)-2,2,2-trifluoro-1-methylethoxy]pyridine (Preparation 236, 560 mg, 1.59 mmol) in acetone (5 mL) was added an aqueous solution of Oxone® (5 mL, 1.24 g, 1.91 mmol) dropwise with stirring at 0° C. for 15 minutes. The reaction mixture was diluted with water and extracted with EtOAc (3×15 mL), the combined organic phases were washed with brine (15 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give a crude product as a brown oil. The crude product was purified by silica gel column chromatography eluting with 0-40% EtOAc in heptane to give the title compound (361 mg, 54%) as yellow oil.

1. extractionextracted with EtOAc (3×15 mL)
2. washthe combined organic phases were washed with brine (15 mL)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated in vacuo
6. customto give a crude product as a brown oil
7. customThe crude product was purified by silica gel column chromatography
8. washeluting with 0-40% EtOAc in heptane