Cesium carbonate → HCID 69670996, compound

HRID 1191660Notes

Reaction equation

HRID 1191660 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=O)=O)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCCC1CO>[CH3:20][S:19][C:15]1[CH:14]=[C:13]2[C:18](=[CH:17][CH:16]=1)[NH:10][C:11]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:12]2

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 69670799HCID 69670799, compound

Product 1

HCID 69670996HCID 69670996, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 7360Tetrahydrofurfuryl alcoholSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-benzenesulfonyl-5-methylsulfanyl-2-phenylindole (264 mg) in tetrahydrofuran-methanol (2/1, 6.9 mL) was added cesium carbonate (680 mg) at room temperature, and the mixture was stirred at 50° C. for 26 hours. The reaction mixture was allowed to cool to ambient temperature and concentrated under reduced pressure. 1 mol/L Hydrochloric acid was added to the residue and this resulting mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (149 mg).

Workup

  1. temperatureto cool to ambient temperature
  2. concentrationconcentrated under reduced pressure
  3. addition1 mol/L Hydrochloric acid was added to the residue
  4. extractionthis resulting mixture was extracted with ethyl acetate
  5. washThe organic layer was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-92f456a1507f44b589652fdbe1833777
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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