Allyl bromide → 2-{3-[2-(4-Chloro-phenyl)-ethyl]-2-methyl-1-allyl-1H-indole-5-yloxy}-2-methyl-propanoic acid ethylester

HRID 66883Notes

Reaction equation

HRID 66883 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH3:18])=[C:12]2[CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)([CH3:7])[CH3:6])[CH3:2].[Na].[H-].[Na+].[CH2:32](Br)[CH:33]=[CH2:34]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:28])[C:5]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:34][CH:33]=[CH2:32])[C:13]([CH3:18])=[C:12]2[CH2:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([Cl:27])=[CH:25][CH:26]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 5360545SodiumHCID 539730412-{3-[2-(4-Chloro-phenyl)-ethyl]-2-methyl-1H-indole-5-yloxy}-2-methyl-propanoic acid ethylester

Product 1

HCID 536951902-{3-[2-(4-Chloro-phenyl)-ethyl]-2-methyl-1-allyl-1H-indole-5-yloxy}-2-methyl-propanoic acid ethylester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Two grams (5 m mole) of 2-{3-[2-(4-chloro-phenyl)-ethyl]-2-methyl-1H-indole-5-yloxy}-2-methyl-propanoic acid ethylester in 20 ml of absolute dimethylformamide were converted to the sodium salt in the present of 0.24 g (~5 m mole) of 55% sodium hydride immersion in oil, and the mixture was alkylated with 1.2 g (10 m mole) of allylbromide at room temperature. After the solvent was distilled off in vacuo, the evaporation residue was dissolved in toluene, filtered, and purified over a silicagel column (solvent: toluene).

Workup

  1. distillationAfter the solvent was distilled off in vacuo
  2. dissolutionthe evaporation residue was dissolved in toluene
  3. filtrationfiltered
  4. custompurified over a silicagel column (solvent: toluene)

Sources & evidence

ORD record
ord-4656a5e689594347ab3bffe983543fa6
Source dataset
uspto-grants-1982_08
Patent number
US04343811

Reaction notes

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