Methyl iodide → HCID 10375132, compound

HRID 1646754Notes

Reaction equation

HRID 1646754 reaction equation
C([NH:4]C(C)C)(C)C.[CH2:8]([Li])[CH2:9][CH2:10][CH3:11].[NH:13]1[C:21]2[C:16](=[CH:17]C=CC=2)[CH:15]=C1CC#N.CI.O1[CH2:31][CH2:30][CH2:29][CH2:28]1>CCCCCC.O>[NH:4]1[C:11]2[C:10](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:9]=[C:8]1[C:16]([CH3:15])([CH3:17])[C:21]#[N:13]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 8028Tetrahydrofuran3×HCID 1697311H-IndoleacetonitrileHCID 178418339Butyllithium

Product 1

HCID 10375132HCID 10375132, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

To a solution of diisopropylamine (809 mg) in tetrahydrofuran (20 ml) at -30° C. under nitrogen atmosphere was added 1.64M butyllithium in hexane (5.33 ml). After being stirred at the same temperature for 30 minutes, the mixture was treated with a solution of indol-2-yl-acetonitrile (1.25 g) in tetrahydrofuran (10 ml) at -60° C. over 15 minutes. The mixture was stirred at the same temperature for an hour, and a solution of methyl iodide (1.14 g) in tetrahydrofuran (10 ml) was added dropwise over an hour. After the mixture was stirred at -60° C. for one hour and at ambient temperature for 2 hours, it was diluted with chilled water, and extracted two times with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by alumina column chromatography (10% ethylacetate-toluene) to give 2-(indol-2-yl)-2-methylpropiononitrile (354 mg).

Workup

  1. stirringThe mixture was stirred at the same temperature for an hour
  2. stirringAfter the mixture was stirred at -60° C. for one hour and at ambient temperature for 2 hours
  3. extractionextracted two times with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by alumina column chromatography (10% ethylacetate-toluene)

Sources & evidence

ORD record
ord-a902f114a47d4aa7b26f1a74da4fda63
Source dataset
uspto-grants-1993_01
Patent number
US05180728

Reaction notes

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