Water → HCID 20084251, compound

HRID 1609220Notes

Reaction equation

HRID 1609220 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:6]2[S:17][C:18]([CH3:21])([CH3:20])[CH3:19].[H-].[Na+].[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Cl)=[CH:27][CH:26]=1.O>CN(C=O)C>[Cl:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[C:6]([S:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[C:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 20084254HCID 20084254, compound

Product 1

HCID 20084251HCID 20084251, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 5-methoxy-3-(t-butylthio)indole-2-carboxylate from step 1 in DMF (50 ml) at 0° C. was added sodium hydride (60% suspension in mineral oil 460 mg, 11.5 mmol). The reaction mixture was stirred at room temperature for 15 minutes, and p-chlorobenzyl chloride (1.93 g, 12.0 mmol) was added. The reaction mixture was stirred at ambient temperature for 14 hours and was then poured into H2O (200 ml) and extracted with ethyl acetate. The organic phase was washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by chromatography on silica gel (8:1 hexane/ethyl acetate) to provide 4.1 g of ethyl 1-(4-chlorobenzyl)-3-(t-butylthio)-5-methoxyindole-2-carboxylate.

Workup

  1. stirringThe reaction mixture was stirred at ambient temperature for 14 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silica gel (8:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6500f2efd49e4a7b8267e3806bb057ae
Source dataset
uspto-grants-1995_03
Patent number
US05399699

Reaction notes

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