Potassium Carbonate → HCID 58980976, compound

HRID 1181804Notes

Reaction equation

HRID 1181804 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:17]([O-:20])([O-])=[O:18].[K+].[K+].BrCC(OC(C)(C)C)=O>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][CH2:1][C:17]([OH:20])=[O:18])(=[O:8])=[O:7])[CH:13]=1)=[O:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 58980924HCID 58980924, compound

Product 1

HCID 58980976HCID 58980976, 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 1.4 g (7.2 mmol) tert-butyl bromoacetate in CH3CN was heated at reflux 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 gave an oil that was chromatographed by normal phase (100% CH2Cl2 followed by gradient elution to 20 EtOAc in CH2Cl2) to give material that was dissolved in 2 mL 1:1 CH2Cl2-TFA with stirring overnight. Solvent was removed to give the title compound as a solid, 1H NMR (DMSO) δ 9.6 (s, 1H), 7.4 (s, 1H), 7.2 (s, 1H), 4.1 (s, 3H), 3.9 (s, 2H).

Workup

  1. temperatureat reflux overnight Solvent
  2. customwas removed
  3. customthe residue was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customDrying
  7. custom(MgSO4) and removal of solvent
  8. customgave an oil that
  9. customwas chromatographed by normal phase (100% CH2Cl2 followed by gradient elution to 20 EtOAc in CH2Cl2)
  10. customto give material that
  11. customSolvent was removed

Sources & evidence

ORD record
ord-38c5d89d0244471fb66859df5e33eb8f
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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