Methanol → 3-Methanesulfonyl-4-(3-methyl-benzo[b]thiophene-2-sulfonylamino)-benzoic acid methyl ester

HRID 1790227Notes

Reaction equation

HRID 1790227 reaction equation
CO.Cl[C:4]1[CH:31]=[CH:30][C:7]2[S:8][C:9]([S:12]([NH:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=3[S:26]([CH3:29])(=[O:28])=[O:27])(=[O:14])=[O:13])=[C:10]([CH3:11])[C:6]=2[CH:5]=1>[Pd].O1CCOCC1>[CH3:11][C:10]1[C:6]2[CH:5]=[CH:4][CH:31]=[CH:30][C:7]=2[S:8][C:9]=1[S:12]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[S:26]([CH3:29])(=[O:28])=[O:27])(=[O:13])=[O:14]

Participants

5

Reactant 2

HCID 887MethanolHCID 101624624-(5-Chloro-3-methyl-benzo[b]thiophene-2-sulfonylamino)-3-methanesulfonyl-benzoic acid methyl ester

Product 1

HCID 120451403-Methanesulfonyl-4-(3-methyl-benzo[b]thiophene-2-sulfonylamino)-benzoic acid methyl esterYield 22.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Into a mixed solvent of 30 mL of methanol and 30 mL of dioxane was dissolved 640 mg of 5% palladium/carbon, followed by 10 minutes of stirring under a hydrogen atmosphere. Under an argon atmosphere, 330 mg of Compound 1 was added, followed by 3 days of stirring under a hydrogen atmosphere at 5 atm. After confirmation of disappearance of the starting material, the reaction mixture was filtered and purified by silica gel column chromatography (ethyl acetate/hexane=2/1) to obtain 70 mg of the title compound as colorless powder.

Workup

  1. waitfollowed by 3 days
  2. stirringof stirring under a hydrogen atmosphere at 5 atm
  3. filtrationAfter confirmation of disappearance of the starting material, the reaction mixture was filtered
  4. custompurified by silica gel column chromatography (ethyl acetate/hexane=2/1)

Sources & evidence

ORD record
ord-dfaf5cab0b8e4e7188a11fb0523060d5
Source dataset
uspto-grants-2006_07
Patent number
US07071220B2

Reaction notes

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