Iodoethane → HCID 69359839, compound

HRID 852654Notes

Reaction equation

HRID 852654 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]1[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[H-].[Na+].[CH2:22](I)[CH3:23]>CN(C=O)C>[CH2:22]([N:11]1[C:12]2[C:8](=[C:7]([N:3]3[CH2:4][CH2:5][CH2:6][C:2]3=[O:1])[CH:15]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[CH:13]=2)[CH:9]=[CH:10]1)[CH3:23]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 69357190HCID 69357190, compound

Product 1

HCID 69359839HCID 69359839, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 4-(2-oxo-1-pyrrolidinyl)-1H-indole-6-carboxylate (B154) (500 mg, 1.94 mmol, 1 equiv) in DMF (10 ml) at room temperature was added NaH (60% dispersion in mineral oil, 84 mg, 2.1 mmol, 1.1 equiv) and the resulting mixture was stirred 15 min. Ethyl iodide (200 μl, 2.5 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 a 2N aqueous HCl solution, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/4 to 1/1) gave methyl 1-ethyl-4-(2-oxo-1-pyrrolidinyl)-1H-indole-6-carboxylate (B140) (400 mg, 72%) as an off-white solid. [M+H]+=287.0, RT=2.73 min.

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 a 2N aqueous HCl solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (AcOEt/iso-hexane: 1/4 to 1/1)

Sources & evidence

ORD record
ord-40c19dcf1d8e4591ab41b34ce825e7ca
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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