Potassium hydroxy sulfite → 5-chloro-6-[(1R)-2,2,2-trifluoro-1-methylethoxy]pyridin-3-ol
Reaction equation
[Cl:1][C:2]1[C:3]([O:17][C@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20])=[N:4][CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.[OH:24]OS([O-])=O.[K+]>CC(C)=O.O>[Cl:1][C:2]1[CH:7]=[C:6]([OH:24])[CH:5]=[N:4][C:3]=1[O:17][C@H:18]([CH3:23])[C:19]([F:22])([F:21])[F:20]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- extractionextracted with EtOAc (3×15 mL)
- washthe combined organic phases were washed with brine (15 mL)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customto give a crude product as a brown oil
- customThe crude product was purified by silica gel column chromatography
- washeluting with 0-40% EtOAc in heptane
Sources & evidence
- ORD record
- ord-d8d14af46e944bf08b9f790257d0fb17
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08592629B2
Reaction notes
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