Chloride → (5-Methoxy-2-methyl-1H-indol-3-yl)(4-methylphenyl)methanone

HRID 505673Notes

Reaction equation

HRID 505673 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[CH:6]2.[C:13]1([CH3:22])[CH:18]=[CH:17][C:16]([C:19](Cl)=[O:20])=[CH:15][CH:14]=1.[Cl-].[Cl-].[NH4+]>ClCCl.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2[C:19]([C:16]1[CH:17]=[CH:18][C:13]([CH3:22])=[CH:14][CH:15]=1)=[O:20]

Participants

7

Reactant 4

HCID 312ChlorideHCID 134054-Methylbenzoyl ChlorideHCID 25517Ammonium ChlorideHCID 706425-Methoxy-2-methylindole

Product 1

HCID 59430875(5-Methoxy-2-methyl-1H-indol-3-yl)(4-methylphenyl)methanoneYield 59%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-methoxy-2-methylindole (816 mg, 5.06 mmol) in dichloromethane (15 ml) were added zinc chloride (1.52 g, 11.14 mmol) and ethyl magnesium bromide diethy ether (3.0 mol/l, 2.02 ml, 6.07 mmol) and the mixture was stirred for 1 hour at room temperature. Thereto was added p-toluoyl chloride (1.25 g, 8.10 mmol). After stirring for 1 hour, thereto was added alminium chloride (337 mg, 2.53 mmol) and the mixture was stirred at room temperature for 20 hours. To the reaction mixture was added an aqueous saturated ammonium chloride solution and the mixture was extracted with chloroform. The organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated brine, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography and by recrystallization to give the subject compound (833 mg, 59%).

Workup

  1. stirringAfter stirring for 1 hour
  2. stirringthe mixture was stirred at room temperature for 20 hours
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with a saturated sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by silica gel column chromatography and by recrystallization

Sources & evidence

ORD record
ord-4dfc8e66bbb14c84bec5bd5fa50835c8
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Reaction notes

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