Methyl iodide → 5-Chloro-2-(2,4-dichlorophenyl)-1-methyl-1H-indole

HRID 966065Notes

Reaction equation

HRID 966065 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]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[CH:5]2.[CH3:19]I.[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:19])[C:6]([C:11]1[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=1[Cl:18])=[CH:5]2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223142515-chloro-2-(2,4-dichlorophenyl)-1H-indole

Product 1

HCID 223143095-Chloro-2-(2,4-dichlorophenyl)-1-methyl-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-chloro-2-(2,4-dichlorophenyl)-1H-indole (160 mg, 0.54 mmol) and methyl iodide (124 μL, 2.0 mmol) in tetrahydrofuran is treated with NaH (60% dispersion in mineral oil, 160 mg, 4.0 mmol), shaken at room temperature for 16 h, quenched with water and extracted with ethyl acetate. The extracts are combined and concentrated in vacuo to afford the title product which is used as is in Example 128.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0a810f776514561beacd2a943070c40
Source dataset
uspto-grants-2005_10
Patent number
US06951881B2

Reaction notes

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