Sodium hydride → Pyridine, 2-(4-nitro-1H-imidazol-1-yl)-
Reaction equation
[N+:1]([C:4]1[N:5]=[CH:6][NH:7][CH:8]=1)([O-:3])=[O:2].[H-].[Na+].[O-]S(C(F)(F)F)(=O)=O.F[N+:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C=O)C>[N+:1]([C:4]1[N:5]=[CH:6][N:7]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)[CH:8]=1)([O-:3])=[O:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
A suspension of 4-nitro-1H-imidazole (0.5 g, 4.4 mmol) in DMF (15 ml) was cooled to 0° C. and treated with sodium hydride (0.23 g, 5.3 mmol). Stirring was continued at 0° C. for 1 h and subsequently cooled to −30° C. A solution of N-fluoropyridinium triflate (0.55 g, 2.2 mmol) in DMF (10 ml) was added within 5 min. After warming-up to ambient temperature, the reaction mixture was stirred at that temperature overnight. The crude product was obtained after extraction with ethyl acetate (2×100 ml), washing of the combined organic phases with 10% aqueous potassium bisulphate solution, water and brine and finally drying and solvent evaporation. This off-white solid material (0.33 g, 39%) was used without any further purification for the next step. MS: M=191.3 (M+H)+
Workup
- temperaturesubsequently cooled to −30° C
- temperatureAfter warming-up to ambient temperature
- stirringthe reaction mixture was stirred at that temperature overnight
Sources & evidence
- ORD record
- ord-b60403879c774e71ba0df2d03700c3b7
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08470820B2
Reaction notes
Loading…