Hydrogen Peroxide → HCID 58042389, Verbindung

HRID 2048037

Reaktionsgleichung

Reaktionsgleichung von HRID 2048037
[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 4, 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-975ab379ebe144bd9d22bd0d886a6f7e
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08592629B2

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