4-Fluorobenzyl bromide → HCID 22485436, compound

HRID 2181007Notes

Reaction equation

HRID 2181007 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:13](=[O:19])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[CH:8][N:9]2[CH3:12])=[CH:5][C:4]=1[C:20]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21].[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33]Br)=[CH:31][CH:30]=1>CCO>[F:28][C:29]1[CH:36]=[CH:35][C:32]([CH2:33][N:25]2[CH2:24][CH2:23][CH:22]([C:20]([C:4]3[CH:5]=[C:6]4[C:10](=[CH:11][C:3]=3[O:2][CH3:1])[N:9]([CH3:12])[CH:8]=[C:7]4[C:13](=[O:19])[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[O:21])[CH2:27][CH2:26]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 680214-Fluorobenzyl bromideHCID 22485450HCID 22485450, compound

Product 1

HCID 22485436HCID 22485436, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

144 mg of 2-[6-Methoxy-1-methyl-5-(piperidine-4-carbonyl)-1H-indol-3-yl]-N,N-dimethyl-2-oxo-acetamide (0.39 mMol) is dissolved in 10 ml EtOH followed by the addition of 0.05 ml of 4-fluorobenzyl bromide (0.4 mMol). The reaction mixture is stirred at room temperature over night. After removing the solvent, residue is taken up in CH2Cl2 and washed with H2O, brine, dried over anhydrous sodium sulfate and concentrated. Silica gel column separation (2% MeOH in CH2Cl2) then gives 133 mg of product.

Workup

  1. customAfter removing the solvent, residue
  2. washwashed with H2O, brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customSilica gel column separation (2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b676b4a6209e492d872485eba56aee26
Source dataset
uspto-grants-2005_05
Patent number
US06890938B2

Reaction notes

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