Potassium peroxymonosulphate → 5-Chloro-6-cyclopropylpyridin-3-OL
Reaction equation
[Cl:1][C:2]1[C:3]([CH:17]2[CH2:19][CH2:18]2)=[N:4][CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.S([O-])(O[O-])(=O)=[O:21].[K+].[K+]>CC(C)=O.O.CC(OC)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([OH:21])[CH:5]=[N:4][C:3]=1[CH:17]1[CH2:19][CH2:18]1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
3-Chloro-2-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 41, 3.092 mmol assuming 100% in previous step) was dissolved in acetone (10.0 mL) and cooled to 0° C. with an ice bath. Then potassium peroxymonosulfate (2.55 g, 4.15 mmol) in water (10.0 mL) was added dropwise to the mixture and stirred at this temperature for 1 hour. The reaction was then diluted in TBME (25.0 mL) and washed with brine (3×25.0 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude product was purified with silica gel chromatography eluting with 0 to 30% EtOAc in heptane to yield the title compound as a pale yellow solid (0.220 g, 1.28 mmol, 42% over 2 steps).
Workup
- washwashed with brine (3×25.0 mL)
- dry with materialThe organic layer was then dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resulting crude product was purified with silica gel chromatography
- washeluting with 0 to 30% EtOAc in heptane
Sources & evidence
- ORD record
- ord-a34fcdbbf675419da01a0c5b5b82f83c
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102621B2
Reaction notes
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