Sodium hydride → 1-[2-(4-Chloro-phenyl)-ethyl]-1H-indole-2-carboxylic acid ethyl ester

HRID 1071673Notes

Reaction equation

HRID 1071673 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:20][CH:19]=1>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylateHCID 2447732-(4-Chlorophenyl)ethyl 4-methylbenzenesulfonate

Product 1

HCID 688562801-[2-(4-Chloro-phenyl)-ethyl]-1H-indole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.5 g (2.6 mmol) of 1H-Indole-2-carboxylic acid ethyl ester was dissolved in DMF and 116 mg (2.9 mmol) of sodium hydride (60% dispersion in mineral oil) was added. The solution was stirred for 30 min at room temperature, then cooled to −78° C. A solution of 0.82 g (2.6 mmol) of toluene-4-sulfonic acid 2-(4-chloro-phenyl)-ethyl ester in DMF was added to this cooled solution. The solution was warmed to RT and was stirred for 16 h. The solvent was removed under reduced pressure, the residue was taken-up in ethyl acetate and the solution was washed once with saturated aqueous sodium bicarbonate, once with water, and once with saturated aqueous sodium chloride. The organic phase was dried with magnesium sulfate, filtered and the solvent was removed under reduced pressure. The residue was chromatographed on silica gel eluting with a gradient of n-heptane/ethyl acetate.

Workup

  1. temperaturecooled to −78° C
  2. temperatureThe solution was warmed to RT
  3. stirringwas stirred for 16 h
  4. customThe solvent was removed under reduced pressure
  5. washthe solution was washed once with saturated aqueous sodium bicarbonate, once with water
  6. dry with materialThe organic phase was dried with magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customThe residue was chromatographed on silica gel eluting with a gradient of n-heptane/ethyl acetate

Sources & evidence

ORD record
ord-437070400e164044b9f427821c0bc1a2
Source dataset
uspto-grants-2005_06
Patent number
US06906084B2

Reaction notes

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