Trimethylsilylmethyl Azide → 2-Bromo-6-(fluoro{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)pyridine

HRID 386067

Reaktionsgleichung

Reaktionsgleichung von HRID 386067
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:11])[C:9]#[CH:10])[N:3]=1.[CH3:12][Si:13]([CH2:16][N:17]=[N+:18]=[N-:19])([CH3:15])[CH3:14].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([F:11])[C:9]2[N:19]=[N:18][N:17]([CH2:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[CH:10]=2)[N:3]=1

Komponenten

7

Edukt 3

HCID 150751Trimethylsilylmethyl AzideHCID 23667548Sodium AscorbateHCID 595259492-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine

Produkt 1

HCID 595258952-Bromo-6-(fluoro{1-[(trimethylsilyl)methyl]-1H-1,2,3-triazol-4-yl}methyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel3×HCID 6386tert-ButanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

2-Bromo-6-(1-fluoroprop-2-yn-1-yl)pyridine (520 mg, 2.43 mmol) and trimethylsilylmethyl azide (377 mg, 2.92 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL). CuSO4.5H2O (30 mg, 0.12 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (96 mg, 0.49 mmol) in water (1.0 mL). The reaction was stirred at room temperature overnight, diluted with saturated NaHCO3, and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated to a brown residue that was purified by flash chromatography (0-30% EtOAc/hexanes) to afford the title compound as a colorless solid.

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated to a brown residue that
  6. customwas purified by flash chromatography (0-30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-91ced9ba13bd4ff0b33a986cbd7427cc
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

Verknüpfte Notizen

Wird geladen…