Trifluoroacetic acid → 5-Iodo-2-methoxy-4,6-dimethylpyridine-3-carbonitrile
Reaction equation
[CH3:1][O:2][C:3]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:4]=1[C:5]#[N:6].FC(F)(F)C(O)=O.[I:20]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[I:20][C:8]1[C:9]([CH3:11])=[N:10][C:3]([O:2][CH3:1])=[C:4]([C:7]=1[CH3:12])[C:5]#[N:6]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-methoxy-4,6-dimethyl-nicotinonitrile (1.0 g, 6.166 mmol) was disolved in 30 mL of anhydrous methylene chloride and then added with 6 mL of trifluoro acetic acid and N-iodosuccinimide (2.2 g, 9.248 mmol) in this order while stirring at 0° C. under the nitrogen atmosphere and then stirred again at room temperature for about 4 hours. The mixture was added with 60 mL of a saturated solution of sodium carbonate and 60 mL of a saturated solution of Na2S2O3 and then extracted twice with 80 mL of methylene chloride. The resulting organic layer was dried with anhydrous sodium sulfate, and filtered. A silica gel column chromatography (5% EtOAc/Hexanes) was performed on the resulting residue and 1.67 g (94%) of 5-iodo-2-methoxy-4,6-dimethyl-nicotinonitrile was obtained in white solid.
Workup
- stirringstirred again at room temperature for about 4 hours
- extractionextracted twice with 80 mL of methylene chloride
- dry with materialThe resulting organic layer was dried with anhydrous sodium sulfate
- filtrationfiltered
Sources & evidence
- ORD record
- ord-56a9e0467fdb4389a6edcbf97db599b3
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07601736B2
Reaction notes
Loading…