N-Iodosuccinimide → HCID 178477819, compound
Reaction equation
[Cl:1][C:2]1[C:3]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:4][NH:5][CH:6]=1.C1C(=O)N([I:20])C(=O)C1>CN(C)C=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Cl:1][C:2]1[C:3]([CH:7]2[CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)=[N:4][NH:5][C:6]=1[I:20]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-chloro-3-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (compound 294.3, 3.00 g, 16.1 mmol) in N,N-dimethylformamide (20 mL) was added NIS (7.26 g, 32.3 mmol). The reaction mixture was stirred overnight at 80° C. The reaction mixture was diluted with 50 mL Na2S2O3 (sat.). The aqueous phase was extracted with 3×100 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/8-1/5) as the eluent to furnish 4.05 g (81%) of the title compound as a white solid.
Workup
- extractionThe aqueous phase was extracted with 3×100 mL of ethyl acetate
- dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by silica gel chromatography with ethyl acetate/petroleum ether (1/8-1/5) as the eluent
Sources & evidence
- ORD record
- ord-c02443453d7a451ebf380cf0ce70a869
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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