Sodium → 3-Nitro 6-(2-pyridylthio) imidazo [1,2-a] pyridine
Reaction equation
[Na].[SH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.Br[C:10]1[CH:11]=[CH:12][C:13]2[N:14]([C:16]([N+:19]([O-:21])=[O:20])=[CH:17][N:18]=2)[CH:15]=1>CN1CCCC1=O>[N+:19]([C:16]1[N:14]2[CH:15]=[C:10]([S:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=3)[CH:11]=[CH:12][C:13]2=[N:18][CH:17]=1)([O-:21])=[O:20]Participants
5
Procedure
A solution of 1.61 g. (0.012 mole) of the sodium salt of 2-mercapto pyridine and 2.42 g. (0.01 mole) of 6-bromo-3-nitroimidazo [1,2-a] pyridine in 10 ml. N-methylpyrolidinone is heated at 150° C. for 40 minutes under a nitrogen atmosphere. The cooled solution is poured onto 100 ml. of ice-water and the resultant suspension is extracted with ethyl acetate. The combined extracts are washed with saturated aqueous sodium chloride and dried over magnesium sulfate. Evaporation of the solvent to a small volume and dilution with N-hexane yields crystalline material. The solids are purified by chromatography on silica gel. Elution with methylene chloride yields pure 3-nitro 6-(2-pyridylthio) imidazo [1,2-a] pyridine.
Workup
- additionThe cooled solution is poured onto 100 ml
- extractionof ice-water and the resultant suspension is extracted with ethyl acetate
- washThe combined extracts are washed with saturated aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- customEvaporation of the solvent to a small volume and dilution with N-hexane
- customyields crystalline material
- customThe solids are purified by chromatography on silica gel
- washElution with methylene chloride
Sources & evidence
- ORD record
- ord-8ccb3b4f8f514fe3ba546d42f7e7c0fb
- Source dataset
- uspto-grants-1979_03
- Patent number
- US04146642
Reaction notes
Loading…