2,4-DICHLOROBENZYL IODIDE → HCID 10131732, compound

HRID 2187737Notes

Reaction equation

HRID 2187737 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[CH:8]2)=[O:4].[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17]I>[Ag]=O.O1CCOCC1>[Cl:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[CH2:17][C:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[NH:10][CH:9]=1

Participants

5

Reactant 2

HCID 5183222,4-DICHLOROBENZYL IODIDEHCID 2737635methyl 1H-indole-5-carboxylate

Product 1

HCID 10131732HCID 10131732, compoundYield 16.4%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

Silver oxide (28.09 g) is added to a dioxane (200 ml) solution of 5-methoxycarbonylindole (17.52 g) and 2,4-dichlorobenzyl iodide (34.49 g), and stirred under reflux for 6.5 hours. The insoluble is removed through filtration, and the filtrate is concentrated under reduced pressure. The resulting oily residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=4/1), and recrystallized from hexane/ethyl acetate to obtain 3-(2,4-dichlorobenzyl)-5-methoxycarbonylindole (46) (5.49 g).

Workup

  1. temperatureunder reflux for 6.5 hours
  2. customThe insoluble is removed through filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe resulting oily residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-eda08ae8faa44142b386686b5c458f26
Source dataset
uspto-grants-2002_06
Patent number
US06410584B1

Reaction notes

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