N-Iodosuccinimide → ethyl 4-iodo-5-methyl-1H-pyrazole-3-carboxylate
Reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[NH:4][N:3]=1.C1C(=O)N([I:19])C(=O)C1>CN(C=O)C>[I:19][C:6]1[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[N:4][NH:3][C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of ethyl 3-methylpyrazole-5-carboxylate (3.11 g, 20.17 mmol) in DMF (50 mL) under Ar at 0° C. was added NIS (5.90 g, 26.2 mmol). The reaction mixture was stirred 20 hr at rt and quenched with 500 mL of water. The resulting precipitate was collected to afford the title product (5.61 g, 20.03 mmol, 99% yield) as a white solid. tR: 3.75 min (HPLC 1); tR: 0.78 min (LC-MS 2); ESI-MS: 281 [M+H]+ (LC-MS 2)
Workup
- customquenched with 500 mL of water
- customThe resulting precipitate was collected
Sources & evidence
- ORD record
- ord-f10b5e2764a14411aa8d29ad518682e2
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08975417B2
Reaction notes
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