Methyl propiolate → Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-4-carboxylate

HRID 2060604

Reaktionsgleichung

Reaktionsgleichung von HRID 2060604
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[N:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Br:17])[N:12]=1)=[N+:8]=[N-:9].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O.C([O-])(O)=O.[Na+].[O-]S([O-])(=O)=O.[Cu+2].O>[Br:17][C:13]1[N:12]=[C:11]([CH2:10][N:7]2[CH:3]=[C:2]([C:1]([O:5][CH3:6])=[O:4])[N:9]=[N:8]2)[CH:16]=[CH:15][CH:14]=1

Komponenten

8

Edukt 3

HCID 13536Methyl propiolateHCID 23667548Sodium AscorbateHCID 453574032-(Azidomethyl)-6-bromopyridine

Produkt 1

HCID 58335253Methyl 1-[(6-bromopyridin-2-yl)methyl]-1H-1,2,3-triazole-4-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 61499Cupric sulfate monohydrateKatalysatorHCID 962WaterLösungsmittel3×HCID 6386tert-ButanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

Methyl propiolate (641 μL, 7.63 mmol) and 2-(azidomethyl)-6-bromopyridine (1.25 g, 5.87 mmol) were combined in t-BuOH (9.0 mL) and water (5.0 mL). A solution of CuSO4.H2O (73 mg, 0.29 mmol) in water (2.0 mL) was added, followed by sodium ascorbate (232 mg, 1.17 mmol) in water (2.0 mL). The reaction was stirred at room temperature for 18 h, during which time it became a yellow suspension. The suspension was diluted with saturated NaHCO3 and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried (MgSO4), and concentrated to dryness. The crude solid was purified by flash chromatography (40-100% ethyl acetate/hexanes) to afford the title compound as a colorless solid. LRMS (APCI) calc'd for C10H10BrN4O2 [M+H]+: 297, Found: 297.

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customThe crude solid was purified by flash chromatography (40-100% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c32ea3739e9a4fdea2d8d0cdf70cbe0f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278335B2

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