Methyl iodide → HCID 69096830, compound

HRID 2409961Notes

Reaction equation

HRID 2409961 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][C:18]3[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][CH:19]=3)=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[H-].[Na+].CI.[C:32](OCC)(=O)C>CN(C)C=O.O>[CH3:32][N:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([CH3:1])[CH:10]=2)[C:6]([CH2:17][C:18]2[N:23]=[C:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20][CH:19]=2)=[C:7]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69096791HCID 69096791, compound

Product 1

HCID 69096830HCID 69096830, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (100 mg) in N,N-dimethylformamide (2 mL) was added sodium hydride (min. 55% in oil, 13 mg) under ice-cooling, and this mixture was stirred at room temperature for 30 minutes. Then, methyl iodide (0.026 mL) was added thereto, followed by stirring at room temperature overnight. To the reaction mixture were added ethyl acetate and water, and the organic layer was separated. The organic layer was washed with water and saturated brine successively, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (35.3 mg). 1H-NMR (CDCl3) δ ppm: 2.51 (3H, s), 3.62 (3H, s), 4.02 (3H, s), 4.36 (2H, s), 6.88-6.95 (1H, m), 7.12-7.20 (2H, m), 7.29 (1H, d, J=8.0 Hz), 7.33-7.49 (5H, m), 7.58 (1H, t, J=7.8 Hz), 7.88-7.95 (1H, m).

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature overnight
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water and saturated brine successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-bbf8326458e847009768849477767846
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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