Reaktion #1098644

Reaktionsgleichung

fluoroazide

1-Azido-3-fluoropropan-2-ol

1-propynyl-2-nitroimidazole

THF

sodium ascorbate

→

pale yellow crystals

Ausbeute 4.2%

1-Fluoro-3-(4-((2-nitro-1H-imidazol-1-yl)methyl)-1H-1,2,3-triazol-1-yl)propan-2-ol

Ausbeute 4.2%

Lösungsmittel

water

t-BuOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe reaction was poured onto EtOAc
2. 2
   Waschenwashed with NH4OH
3. 3
   Sonstigethe material was then purified on a silica gel column
4. 4
   SonstigeThe material was then further purified via recrystallization

Vorschrift

To a vial was added fluoroazide 17 (690 mg, 5.79 mmol) and 1-propynyl-2-nitroimidazole (876 mg, 5.79 mmol). To this flask was added THF (3 mL), t-BuOH (3 mL), water (3 mL), CuSO4 (185 mg, 1.16 mmol) and sodium ascorbate (1.15 g, 5.79 mmol). After 16 hrs, the reaction was poured onto EtOAc and washed with NH4OH. The organics were combined and the material was then purified on a silica gel column using EtOAc:Hex as the eluent. The material was then further purified via recrystallization using EtOAc:Hex to afford 65 mg (4% yield) of pale yellow crystals. 1H NMR (DMSO-d6, 400 MHz), δ: 4.04 (1H, br d, J=20.4 Hz), 4.20-4.47 (4H, m), 5.53 (1H, br s), 5.66 (2H, s), 7.16, (1H, s), 7.68 (1H, s), 8.05 (1H), s).

Quelle