Dimethylformamide → 3-(2,4-Dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile
Reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[S:7].Br[C:9]1[CH:10]=[C:11]([O:17][C:18]2[C:19]([CH3:25])=[N:20][CH:21]=[CH:22][C:23]=2[CH3:24])[C:12]([C:15]#[N:16])=[N:13][CH:14]=1.CN(C=O)C.[H-].[Na+]>O>[CH3:25][C:19]1[C:18]([O:17][C:11]2[C:12]([C:15]#[N:16])=[N:13][CH:14]=[C:9]([S:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[CH:10]=2)=[C:23]([CH3:24])[CH:22]=[CH:21][N:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Pyridine-2(1H)-thione (0.768 g, 6.90 mmol) and 5-bromo-3-(2,4-dimethylpyridin-3-yloxy)picolinonitrile (2.00 g, 6.58 mmol) were added to DMF (12 mL) and cooled to 0° C. 95% Sodium hydride (0.174 g, 6.90 mmol) was slowly added and the reaction was warmed to ambient temperature and stirred overnight. The reaction mixture was poured into water (100 mL) and stirred for 30 minutes. A cloudy milky solution that was not filterable resulted. The reaction was extracted twice with ethyl acetate. The combined organic layers were washed twice with water and brine, dried, and concentrated. The residue was purified over silica gel (2:3 to 0:1 hexane:ethyl acetate) to afford 3-(2,4-dimethylpyridin-3-yloxy)-5-(pyridin-2-ylthio)picolinonitrile (2.03 g, 6.07 mmol, 92.3% yield) as a white powder.
Workup
- temperaturethe reaction was warmed to ambient temperature
- stirringstirred for 30 minutes
- extractionThe reaction was extracted twice with ethyl acetate
- washThe combined organic layers were washed twice with water and brine
- customdried
- concentrationconcentrated
- customThe residue was purified over silica gel (2:3 to 0:1 hexane:ethyl acetate)
Sources & evidence
- ORD record
- ord-f302ac092aab4cc1b7fe1c9eff03bd59
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08853409B2
Reaction notes
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