N-Iodosuccinimide → ethyl 4-iodo-5-methyl-1H-pyrazole-3-carboxylate

HRID 873791Notes

Reaction equation

HRID 873791 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

HCID 120273N-IodosuccinimideHCID 178469061HCID 178469061, compound

Product 1

HCID 60136608ethyl 4-iodo-5-methyl-1H-pyrazole-3-carboxylateYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customquenched with 500 mL of water
  2. 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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