Reaction #1244279

Reaction equation

10

2-Nitro-1-(prop-2-ynyl)-1H-imidazole

29

2-Azido-3-fluoropropan-1-ol

THF

sodium ascorbate

→

1

Yield 88.1%

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

Yield 88.1%

Solvents

t-BuOH

H2O

Conditions

Workup

1. 1
   OtherOrganic solvents removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in CH2Cl2
3. 3
   Washconsecutively washed with H2O
4. 4
   Dryingbrine, then dried over MgSO4
5. 5
   ConcentrationThe solvent was then concentrated in vacuo
6. 6
   Otherthe residue was purified on silica gel using 10% MeOH

Procedure

A solution of 10 (1.9 g, 12.6 mmol) and 29 (1.5 g, 12.6 mmol) in t-BuOH:THF:H2O (22.5 mL, 1:1:1) was treated with CuSO4.5H2O (0.31 g, 1.26 mmol) and sodium ascorbate (0.5 g, 2.52 mmol) and stirred for 1 hr at room temperature. Organic solvents removed under vacuum, the residue dissolved in CH2Cl2 and consecutively washed with H2O, then brine, then dried over MgSO4. The solvent was then concentrated in vacuo and the residue was purified on silica gel using 10% MeOH:CH2Cl2 as the solvent to afford 1 (3.00 g, 88%) as white solid. The product was further purified via recrystallization from EtOAc/hexanes. 1H NMR ((CD3)2CO, 400 MHz) δ: 8.15 (s, 1H), 7.57 (d, J=1.2 Hz, 1H), 7.11 (d, J=1.2 Hz, 1H), 5.79 (s, 2H), 4.87-5.05 (m, 2H), 4.82 (dd, J=4.0, 10.0 Hz, 1H), 4.17-4.45 (m, 1H), 4.03 (t, J=5.6 Hz, 2H). 13C NMR ((CD3)2CO, 100 MHz) δ: 141.8, 127.9, 127.1, 123.5, 83.0, 81.3, 63.0 (d, J=18.69 Hz, 1C), 60.5 (d, J=6.73 Hz, 1C), δ: 44.8; 19F NMR ((CD3)2CO, 376 MHz) 230.2 (ddd, J=19.18, 19.55, 21.60 Hz, IF); Mass Spec (lo-res): Calc'd for C9H11FN6O3: 270.09; found: 271.1 (M+H).

Source