N-Iodosuccinimide → HCID 90029355, compound

HRID 1488216Notes

Reaction equation

HRID 1488216 reaction equation
[CH3:1][N:2]([CH3:11])[C:3]([C:5]1[C:9]([CH3:10])=[CH:8][NH:7][N:6]=1)=[O:4].C1C(=O)N([I:19])C(=O)C1>CC#N>[I:19][C:8]1[NH:7][N:6]=[C:5]([C:3]([N:2]([CH3:11])[CH3:1])=[O:4])[C:9]=1[CH3:10]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178430912HCID 178430912, compound2×

Product 1

HCID 90029355HCID 90029355, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of N,N,4-trimethyl-1H-pyrazole-3-carboxamide (compound 374.1, 0.98 g, 6.40 mmol) in CH3CN (10 mL) was added NIS (1.59 g, 7.04 mmol). The mixture was stirred at room temperature for 16 hours then quenched with sat. Na2SO3 solution (5 mL). The mixture was partitioned between EtOAc (200 mL) and water (30 mL). The EtOAc layer was washed with brine (30 mL), dried (MgSO4) and concentrated. The residue was purified with column chromatography (50% EtOAc in hexanes to 100% EtOAc) to give the product as a brown solid (1.79 g, 100%). m/z (ES+) 280 (M+H)+.

Workup

  1. customthen quenched with sat. Na2SO3 solution (5 mL)
  2. customThe mixture was partitioned between EtOAc (200 mL) and water (30 mL)
  3. washThe EtOAc layer was washed with brine (30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue was purified with column chromatography (50% EtOAc in hexanes to 100% EtOAc)

Sources & evidence

ORD record
ord-78ecb7e6aa7a43af8410f61e80096ae9
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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