Acetic acid, azido-, ethyl ester → ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

HRID 386062

Reaktionsgleichung

Reaktionsgleichung von HRID 386062
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]#[CH:9])[N:3]=1.[N:10]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N+:11]=[N-:12].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][N:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[N:3]=2)[N:12]=[N:11]1)[CH3:18]

Komponenten

7

Edukt 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 129705322-Bromo-6-ethynylpyridineHCID 23667548Sodium Ascorbate

Produkt 1

HCID 59525977ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

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 ethyl azidoacetate (1.08 ml, 1.92 mmol) were combined in t-BuOH (4.0 mL) and water (2.0 mL). CuSO4.5H2O (24 mg, 0.096 mmol) in water (1.0 mL) was added, followed by sodium ascorbate (76 mg, 0.39 mmol) in water (1.0 mL). The reaction was stirred at room temperature for 5 h, 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 (0-30% 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 yellow residue that
  6. customwas purified by flash chromatography (0-30% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c07ac8fa129843fba3c3213505dc47fb
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

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