Methyl iodide → 1-(5-chloro-1-methyl-1H-indol-2-yl)heptan-1-one

HRID 2091301Notes

Reaction equation

HRID 2091301 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2.[H-].[Na+].[CH3:21]I.[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:21])[C:6]([C:11](=[O:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5]2

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66777278HCID 66777278, compound

Product 1

HCID 667777681-(5-chloro-1-methyl-1H-indol-2-yl)heptan-1-oneYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution (10 mL) of 1-(5-chloro-1H-indol-2-yl)heptan-1-one (1.00 g) synthesized in Example A106(2) in N,N-dimethylformamide was added sodium hydride (60%, oily, 182 mg) at 0° C. and the mixture was stirred under argon atmosphere for 30 min. After stirring, methyl iodide (354 μL) was added. The reaction mixture was stirred at room temperature overnight, saturated aqueous ammonium chloride solution was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane to give the title object compound (367 mg, 35%) as a pale-brown solid.

Workup

  1. stirringAfter stirring
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. customto quench
  4. customthe reaction
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-b0737de42eb240fdb6c852451d574ebb
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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