Iodoethane → HCID 54204190, compound

HRID 1901566Notes

Reaction equation

HRID 1901566 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:14]=2)[NH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:29](I)[CH3:30]>CN(C)C=O>[CH2:29]([N:1]1[CH2:5][CH2:4][CH2:3][C@@H:2]1[CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH2:16][CH2:17][S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:14]=2)[NH:9][CH:8]=1)[CH3:30]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 22873790HCID 22873790, compound

Product 1

HCID 54204190HCID 54204190, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of (R)-3-(pyrrolidin-2-ylmethyl)-5-(2-ethylsulphonylethyl)-1H-indole (0.27 g, 0.8 mmol) in dimethylformamide (dried over 4A sieves) (5 mls), was added sodium carbonate (90 mgs) and ethyl iodide (0.07 mls, 0.88 mmol) at room temperature. The mixture was heated at 120° C. under nitrogen for 16 hours. After cooling to room temperature the reaction mixture was partitioned between ethyl acetate and water. The separated organic phase was washed with water (3×), dried (Na2SO4) and evaporated in vacuo to give an oil. Purification by column chromatography on silica gel, eluting with CH2Cl2 :EtOH:NH4OH (90:10:0.5) gave the title compound as a gum (100 mgs). Anal. Calcd for C19H28N2O2S· 1/4CH2Cl2. 1/2H2O: C,61.04; H,7.85; N,7.40. Found: C,60.80; H,7.69; N,7.48⟦alpha⟧sup.25D =+60° (c=0.1, MeOH).

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas partitioned between ethyl acetate and water
  3. washThe separated organic phase was washed with water (3×)
  4. dry with materialdried (Na2SO4)
  5. customevaporated in vacuo
  6. customto give an oil
  7. customPurification by column chromatography on silica gel
  8. washeluting with CH2Cl2 :EtOH:NH4OH (90:10:0.5)

Sources & evidence

ORD record
ord-76e8e5d1a8354964b20fb8927b573b1a
Source dataset
uspto-grants-1996_11
Patent number
US05578612

Reaction notes

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