Sodium Methoxide → t-Butyl 3-phenyl-1-(p-toluenesulfonyl)indole-2-carboxylate

HRID 1871818Notes

Reaction equation

HRID 1871818 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]([CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[S:16]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)(=[O:18])=[O:17])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[C:2]1([C:1]2[C:9]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:15]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:17])=[O:18])[C:26]=2[C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18688807t-Butyl N-(2-benzoylphenyl)-N-(p-toluenesulfonyl)aminoacetate

Product 1

HCID 18688802t-Butyl 3-phenyl-1-(p-toluenesulfonyl)indole-2-carboxylateYield 115.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2.30 g of compound I in 175 cc of methanol was added 0.39 g of sodium methoxide at room temperature and the mixture was stirred for 16 hours. The methanol was distilled off and to the residue was added water, followed by extraction with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The resulting crude product was dissolved in 50 cc of benzene, followed by adding dropwise thereto 1.41 cc of pyridine and then 0.52 g of thionyl chloride at room temperature, and the resulting mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent the crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/4) to obtain 2.55 g of compound J. Yield: 80.2%.

Workup

  1. distillationThe methanol was distilled off and to the residue
  2. additionwas added water
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. dissolutionThe resulting crude product was dissolved in 50 cc of benzene
  8. additionby adding dropwise
  9. stirring1.41 cc of pyridine and then 0.52 g of thionyl chloride at room temperature, and the resulting mixture was stirred at room temperature for 1 hour
  10. additionWater was added to the reaction mixture
  11. extractionextracted with ethyl acetate
  12. dry with materialThe extract was dried over magnesium sulfate
  13. distillationdistilled
  14. customto remove the solvent the crude product
  15. customthus obtained
  16. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-a881e6cca260493796f869e621065968
Source dataset
uspto-grants-2000_08
Patent number
USRE036832

Reaction notes

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