Trimethylsilylmethyl Azide → HCID 59525901, Verbindung

HRID 386059

Reaktionsgleichung

Reaktionsgleichung von HRID 386059
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[N:3]=1.[CH3:10][Si:11]([CH2:14][N:15]=[N+:16]=[N-:17])([CH3:13])[CH3:12].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]([C:8]2[N:17]=[N:16][N:15]([CH2:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[CH:9]=2)[N:3]=1

Komponenten

7

Edukt 3

HCID 150751Trimethylsilylmethyl AzideHCID 129705322-Bromo-6-ethynylpyridineHCID 23667548Sodium Ascorbate

Produkt 1

HCID 59525901HCID 59525901, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

2-Bromo-6-ethynylpyridine (Example 465, Step 1) (350 mg, 1.92 mmol) and trimethylsilylmethyl azide (323 mg, 2.50 mmol) were combined in t-BuOH (4.0 mL) and water (3.0 mL). CuSO4.5H2O (24 mg, 0.096 mmol) in water (0.50 mL) was added, followed by sodium ascorbate (76 mg, 0.39 mmol) in water (0.50 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 yellow residue that was purified by flash chromatography (0-50% 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 yellow residue that
  6. customwas purified by flash chromatography (0-50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-2302a702b83c454e84c00efd094b899a
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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