Methyl iodide → HCID 58980947, compound

HRID 1181803Notes

Reaction equation

HRID 1181803 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:13]=[C:12]([CH:14]=[O:15])[N:11]([CH3:16])[CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C([O-])([O-])=O.[K+].[K+].CI>CC#N.C(Cl)Cl.FC(C(O)=O)(F)F>[CH:14]([C:12]1[N:11]([CH3:16])[CH:10]=[C:9]([S:6]([NH:5][CH3:1])(=[O:8])=[O:7])[CH:13]=1)=[O:15]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 58980924HCID 58980924, compound

Product 1

HCID 58980947HCID 58980947, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 0.8 g (3.3 mmol) N-(tert-butyl)-5-formyl-1-methyl-1H-pyrrole-3-sulfonamide, 1.2 g (9.8 mmol) K2CO3 and 1 mL (16 mmol) CH3I in CH3CN was heated at 60° C. overnight. Solvent was removed, and the residue was partitioned between EtOAc and water. The organic layer was separated and washed with brine. Drying (MgSO4) and removal of solvent to give material that slowly solidified. The material was dissolved in 2 mL 1:1 CH2Cl2-TFA with stirring for 3 h. Solvent was removed to give the title compound as a solid, 1H NMR (DMSO) δ 9.8 (s, 1H), 7.9 (s, 1H), 7.45 (s, 1H), 7.4 (s, 1H), 4.1 (s, 3H), 2.6 (s, 3H).

Workup

  1. customSolvent was removed
  2. customthe residue was partitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customDrying
  6. custom(MgSO4) and removal of solvent
  7. customto give material that
  8. customSolvent was removed

Sources & evidence

ORD record
ord-bb07b36f38b44cadba73c36b5182ade9
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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