1,6-Dibromohexane → 1-(6-Bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indole

HRID 654069Notes

Reaction equation

HRID 654069 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1)=[C:8]2[CH3:22].[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br>CN(C)C=O>[Br:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][N:10]1[C:11]2[C:7](=[CH:6][C:5]([O:4][CH3:3])=[CH:13][CH:12]=2)[C:8]([CH3:22])=[C:9]1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 123681,6-DibromohexaneHCID 24758Sodium hydrideHCID 108800612-(4-METHOXYPHENYL)-3-METHYL-5-METHOXYINDOLE

Product 1

HCID 159256341-(6-Bromohexyl)-5-methoxy-2-(4-methoxyphenyl)-3-methyl-1H-indoleYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

12.5 mmol (300 mg) of NaH are added to 40 ml of absolute dimethylformamide and cooled to 0° C. With vigorous stirring, 7.5 mmol of 5-methoxy-2-(4-methoxy-phenyl)-3-methyl-indole dissolved in 25 ml of absolute dimethylformamide are slowly added dropwise and stirred for 30 minutes at 0° C. This suspension is added dropwise with stirring and ice-cooling to a solution of 11.0 mmol of 1,6-dibromohexane in 25 ml of absolute dimethylformamide and stirred for 30 minutes at 0° C. Excess NaH is destroyed with water and stirring continues for a further 2.5 hours at room temperature. The mixture is shaken with dichloromethane, dried over MgSO4 and the solvent removed. The brown oily crude product is chromatographed on silica gel with dichloro-methane and recrystallized from ethanol. Yield 84%. M.P. 60° C.

Workup

  1. additionare slowly added dropwise
  2. additionThis suspension is added dropwise
  3. stirringwith stirring
  4. stirringstirred for 30 minutes at 0° C
  5. customExcess NaH is destroyed with water
  6. stirringstirring
  7. waitcontinues for a further 2.5 hours at room temperature
  8. stirringThe mixture is shaken with dichloromethane
  9. dry with materialdried over MgSO4
  10. customthe solvent removed
  11. customThe brown oily crude product is chromatographed on silica gel with dichloro-methane
  12. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3f3f18ed38b441208d2bf4260001c89a
Source dataset
uspto-grants-1992_07
Patent number
US05130308

Reaction notes

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