Methyl iodide → HCID 67187925, compound

HRID 868841Notes

Reaction equation

HRID 868841 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([CH2:11][C:12]#[N:13])=[CH:5][NH:6]2.[H-].[Na+].[CH3:16]I>C1COCC1>[CH3:16][N:6]1[C:7]2[C:3](=[C:2]([CH3:1])[CH:10]=[CH:9][CH:8]=2)[C:4]([CH2:11][C:12]#[N:13])=[CH:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24905095(4-Methyl-1H-indol-3-yl)acetonitrile

Product 1

HCID 67187925HCID 67187925, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(4-Methyl-1H-indol-3-yl)-acetonitrile (540 mg, 3.2 mmol), is taken up in dry THF (10.3 mL), cooled to zero, and sodium hydride (228 mg, 60% in mineral oil, 6 mmol) is added to the stirring solution. The reaction is stirred for 15 minutes at zero and methyl iodide (0.26 mL, 4 mmol) is added. The solution is stirred for 20 minutes at zero, and quenched by the slow addition of saturated aqueous ammonium chloride. The compound is extracted with ethyl acetate, dried (Na2SO4), filtered, and evaporated in vacuo to give a solid that is purified on silica gel with hexanes/ethylacetate as the eluent (1.0 g, 5 mmol, 71%) LC/MS (M++1): 185.5.

Workup

  1. additionis added to the stirring solution
  2. additionis added
  3. customquenched by the slow addition of saturated aqueous ammonium chloride
  4. extractionThe compound is extracted with ethyl acetate
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto give a solid

Sources & evidence

ORD record
ord-cdd4ee6bdc2e43699447f90c028d08f6
Source dataset
uspto-grants-2015_03
Patent number
US08969348B2

Reaction notes

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