Hydrogen Peroxide → HCID 58042389, Verbindung

HRID 512061

Reaktionsgleichung

Reaktionsgleichung von HRID 512061
[Cl:1][C:2]1[C:3]([O:17][CH2:18][CH:19]2[CH2:22][C:21]([F:24])([F:23])[CH2:20]2)=[N:4][CH:5]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:7]=1.OO.S([O-])([O-:29])=S>CO>[Cl:1][C:2]1[CH:7]=[C:6]([OH:29])[CH:5]=[N:4][C:3]=1[O:17][CH2:18][CH:19]1[CH2:22][C:21]([F:24])([F:23])[CH2:20]1

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 9548651Thiosulfite(2-)HCID 580424833-Chloro-2-((3,3-difluorocyclobutyl)methoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)pyridine

Produkt 1

HCID 58042389HCID 58042389, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3-Chloro-2-[(3,3-difluorocyclobutyl)methoxy]-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 38, 4.5 g, 12.5 mmol) was suspended in methanol (30 mL). Hydrogen peroxide (1.6 mL, 21.3 mmol) was added and the mixture stirred at room temperature under nitrogen for 16 hours. An aqueous solution of thiosulfite (10%, 10 mL) was added and the mixture was extracted with EtOAc (2×200 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane) to afford the title compound (2.53 g, 81%).

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc (2×200 mL)
  2. dry with materialThe combined organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel chromatography (Biotage®, gradient of 0-50% EtOAc in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-760529be6cd646738e14bb8ab900c714
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102621B2

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