Potassium Carbonate → (S)-5-ethynyl-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide
Reaction equation
[CH3:1][S@:2](=[O:24])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[N:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]#[C:12][Si](C)(C)C)[CH:8]=[N:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[C:11]([C:9]1[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=1)[C:4]([N:3]=[S@@:2]([CH3:1])(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:17])#[CH:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (S)—N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (806 mg, 2.3 mmol) in 70 mL THF/methanol (1:1 ratio) at room temperature was degassed with argon. The solution was cooled to 0° C. and K2CO3 (937 mg, 6.8 mmol) added. After 5 minutes the solution was decanted from the solids and partitioned between EtOAc and H2O. The EtOAc layer was washed with brine, dried with anhydrous Na2SO4 and concentrated. The brown oil was purified by chromatography (silica gel, CHCl3/EtOAc) to the title compound as a thick pale orange oil (630 mg, 98%).
Workup
- customAfter 5 minutes the solution was decanted from the solids
- custompartitioned between EtOAc and H2O
- washThe EtOAc layer was washed with brine
- dry with materialdried with anhydrous Na2SO4
- concentrationconcentrated
- customThe brown oil was purified by chromatography (silica gel, CHCl3/EtOAc) to the title compound as a thick pale orange oil (630 mg, 98%)
Sources & evidence
- ORD record
- ord-4000a6d7cbc24f66983af6f2aa3b12c0
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08143410B2
Reaction notes
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