Potassium peroxymonosulphate → 5-Chloro-6-cyclopropylpyridin-3-OL

HRID 512063Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 512063
[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]1

Komponenten

6

Edukt 2

HCID 10313463Potassium peroxymonosulphateHCID 58042381(5-Chloro-6-cyclopropylpyridin-3-yl)boronic acid pinacol ester

Produkt 1

HCID 580424875-Chloro-6-cyclopropylpyridin-3-OLAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. washwashed with brine (3×25.0 mL)
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude product was purified with silica gel chromatography
  6. washeluting with 0 to 30% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-a34fcdbbf675419da01a0c5b5b82f83c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102621B2

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