N-Iodosuccinimide → HCID 90029866, compound
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:8]#[N:9])=[N:5][NH:6][CH:7]=1.C1C(=O)N([I:17])C(=O)C1>CN(C)C=O>[I:17][C:7]1[NH:6][N:5]=[C:4]([C:8]#[N:9])[C:3]=1[O:2][CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 4-methoxy-1H-pyrazole-3-carbonitrile (compound 280.7, 200 mg, 1.62 mmol) in N,N-dimethylformamide (15 mL) was added NIS (549 mg, 2.44 mmol). The reaction mixture was stirred for 2 h at 70° C., then quenched with 20 mL of Na2S2O3 (sat.). The aqueous phase was extracted with 2×50 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 (1:6) as the eluent to furnish 330 mg (82%) of the title compound as a white solid.
Workup
- customquenched with 20 mL of Na2S2O3 (sat.)
- extractionThe aqueous phase was extracted with 2×50 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 (1:6) as the eluent
Sources & evidence
- ORD record
- ord-4c7977b74fd84bc59f3849221c7d4958
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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