Iodoethane → HCID 69358242, compound

HRID 852655Notes

Reaction equation

HRID 852655 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[C:7]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[NH:5][CH:4]=1)[CH3:2].[H-].[Na+].[CH2:25](I)C>CN(C=O)C>[CH2:1]([C:3]1[C:11]2[C:6](=[C:7]([N:17]3[CH2:21][CH2:20][CH2:19][C:18]3=[O:22])[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[N:5]([CH3:25])[CH:4]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69359522HCID 69359522, compound

Product 1

HCID 69358242HCID 69358242, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 3-ethyl-7-(2-oxo-1-pyrrolidinyl)-1H-indole-5-carboxylate (B141) (658 mg, 2.3 mmol, 1 equiv) in DMF (10 ml) at room temperature was added NaH (60% dispersion in mineral oil, 120 mg, 3.0 mmol, 1.3 equiv) and the resulting mixture was stirred 15 min at this temperature. Ethyl iodide (187 μl, 3.0 mmol, 1.3 equiv) was added and the resulting solution was stirred for 30 min then concentrated in vacuo. The residue was dissolved in AcOEt and the organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. The residue was triturated with iso-hexane to give ethyl 3-ethyl-1-methyl-7-(2-oxo-1-pyrrolidinyl)-1H-indole-5-carboxylate (620 mg, 90%) as a yellow solid which was used in the next step without further purification.

Workup

  1. stirringthe resulting solution was stirred for 30 min
  2. concentrationthen concentrated in vacuo
  3. dissolutionThe residue was dissolved in AcOEt
  4. washthe organic phase was washed with H2O
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with iso-hexane

Sources & evidence

ORD record
ord-daa55e32bf984901a97cae9935fb1b1c
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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