Benzyl Bromide → 2-Benzyloxy-4-(5-methanesulfonyl-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine

HRID 500548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 500548
[CH3:1][S:2]([C:5]1[N:6]([CH3:17])[C:7]([C:10]2[CH:15]=[CH:14][NH:13][C:12](=[O:16])[CH:11]=2)=[N:8][N:9]=1)(=[O:4])=[O:3].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=O)([O-])[O-].[Ag+].[Ag+]>[CH2:18]([O:16][C:12]1[CH:11]=[C:10]([C:7]2[N:6]([CH3:17])[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:9][N:8]=2)[CH:15]=[CH:14][N:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

4

Edukt 2

HCID 7498Benzyl BromideHCID 248518134-(5-Methanesulfonyl-4-methyl-4H-[1,2,4]triazol-3-yl)-1H-pyridin-2-one

Produkt 1

HCID 248517062-Benzyloxy-4-(5-methanesulfonyl-4-methyl-4H-[1,2,4]triazol-3-yl)-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 92796Silver carbonateKatalysator

Versuchsvorschrift

The title compound from example 27.1 (0.95 g, 3.7 mmol) and silver (1) carbonate (1.23 g, 4.48 mmol) were combined in a round bottom flask and purged with nitrogen. Toluene (10 mL) was added, followed by benzyl bromide (0.53 mL, 4.48 mmol) and the reaction was stirred for 72 h at room temperature. The silver salts were then removed by filtration through diatomaceous earth, which were then washed with dichloromethane. The filtrate was concentrated then purified by column chromatography on silica gel with 0-10% ethyl acetate in dichloromethane to give the title compound (off-white solid, 549 mg, 43

Aufarbeitung

  1. custompurged with nitrogen
  2. additionToluene (10 mL) was added
  3. customThe silver salts were then removed by filtration through diatomaceous earth, which
  4. washwere then washed with dichloromethane
  5. concentrationThe filtrate was concentrated
  6. customthen purified by column chromatography on silica gel with 0-10% ethyl acetate in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-c594830b7e894e8e818b093cfa0ed23e
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772235B2

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