Hydrochloric Acid → HCID 68555576, compound

HRID 2382077Notes

Reaction equation

HRID 2382077 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:6]=1I)[CH:2]=[CH2:3].Cl>CN(C=O)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][S:11]([C:8]1[CH:7]=[C:6]2[C:5](=[CH:10][CH:9]=1)[NH:4][CH:1]=[C:2]2[CH3:3])(=[O:13])=[O:12]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68558099HCID 68558099, compound

Product 1

HCID 68555576HCID 68555576, compoundYield 43.1%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of allyl-(2-iodo-4-methanesulfonyl-phenyl)-amine (1.43 g, 4.1 mmol) in DMF (20 mL) is treated with n-Bu4NCl (1.47 g, 5.32 mmol), Pd(OAc)2 (56.6 mg, 0.2 mmol), and stirred at 100° C. for 1 h. HCl (5.3 mL, 3 M) is added, and the mixture is cooled to rt, filtered through a pad of Celite, and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 60% EtOAc in heptane to afford 5-methanesulfonyl-3-methyl-1H-indole (370 mg, 43%).

Workup

  1. temperaturethe mixture is cooled to rt
  2. filtrationfiltered through a pad of Celite
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialThe combined organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel chromatography
  8. washeluting with 60% EtOAc in heptane

Sources & evidence

ORD record
ord-ed47e202967d42ca9f695da020fe95ad
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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