Sodium methanethiolate → 6-Methylsulfanyl-[2,2']bipyridin-3-ol
Reaction equation
F[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]([O:14]C)=[CH:4][CH:3]=1.[CH3:16][S-:17].[Na+]>CN(C)C=O>[CH3:16][S:17][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]([OH:14])=[CH:4][CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
6-Fluoro-3-methoxy-[2,2′]bipyridine (12 mg) and sodium thiomethoxide (41 mg) were suspended in N,N-dimethylformamide (1.5 ml), and the suspension was stirred at 160° C. overnight. The reaction solution was cooled to room temperature, the reaction solution was then filtered, and the solvent was removed from the filtrate by distillation under the reduced pressure. The residue was purified by thin layer chromatography using acetone-chloroform to give 6-methylsulfanyl-[2,2′]bipyridin-3-ol (6 mg, yield 47%).
Workup
- temperatureThe reaction solution was cooled to room temperature
- filtrationthe reaction solution was then filtered
- customthe solvent was removed from the filtrate by distillation under the reduced pressure
- customThe residue was purified by thin layer chromatography
Sources & evidence
- ORD record
- ord-fca730f4c80049ef8a80896a37a8cb98
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07560558B2
Reaction notes
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