Trimethylsilyl iodide → HCID 18797333, compound

HRID 1457009Notes

Reaction equation

HRID 1457009 reaction equation
C1(C[O:5][C:6]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:7]=2[C:8]([C:15]2[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=2)=[CH:9][NH:10]3)CC1.C[Si](I)(C)C>C(#N)C>[OH:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([C:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH:20]=1)=[CH:9][NH:10]2

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 21268233HCID 21268233, compound

Product 1

HCID 18797333HCID 18797333, compoundYield 14.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.30 gm (1.1 mMol) 4-cyclopropylmethoxy-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole in 10 mL acetonitrile were added 0.64 mL (4.4 mMol) trimethylsilyliodide and the reaction mixture was allowed to stir at room temperature for 18 hours. The reaction mixture was concentrated under reduced pressure and the residue partitioned between dilute ammonium hydroxide and ethyl acetate. The phases were separated and the aqueous phase extracted well with ethyl acetate. The organics were combined, washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to radial chromatography, eluting with 15% methanol in dichloromethane containing a trace of ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to provide 0.035 gm (14%) of the title compound as a light tan solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue partitioned between dilute ammonium hydroxide and ethyl acetate
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted well with ethyl acetate
  5. washwashed with saturated aqueous sodium chloride
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting with 15% methanol in dichloromethane containing a trace of ammonium hydroxide
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-caf89c9105aa4b96a101a095f5f09605
Source dataset
uspto-grants-1998_12
Patent number
US05846982

Reaction notes

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