1-Chloro-4-(chloromethyl)benzene → Methyl alpha-[N-methyl-3-(trifluoromethyl)benzylamino]-1-(4-chlorobenzyl)indole-3-acetate

HRID 5611

Reaction equation

HRID 5611 reaction equation
[H-].[Na+].[F:3][C:4]([F:28])([F:27])[C:5]1[CH:6]=[C:7]([CH:24]=[CH:25][CH:26]=1)[CH2:8][NH:9][CH:10]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)[C:11]([O:13][CH3:14])=[O:12].[Cl:29][C:30]1[CH:37]=[CH:36][C:33]([CH2:34]Cl)=[CH:32][CH:31]=1.[CH3:38]CCCCC.C(OCC)(=O)C>CN(C)C=O.CCOCC>[CH3:38][N:9]([CH2:8][C:7]1[CH:24]=[CH:25][CH:26]=[C:5]([C:4]([F:3])([F:27])[F:28])[CH:6]=1)[CH:10]([C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:34][C:33]2[CH:36]=[CH:37][C:30]([Cl:29])=[CH:31][CH:32]=2)[CH:16]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

7

Reactant 4

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 19796632Methyl alpha-[3-(trifluoromethyl)benzylamino]-indole-3acetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 19796715Methyl alpha-[N-methyl-3-(trifluoromethyl)benzylamino]-1-(4-chlorobenzyl)indole-3-acetate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a magnetically stirred suspension of sodium hydride (60% oil dispersion washed two times with hexane, 80 mg, 2.0 mmol) in 5 mL of dimethylformamide (DMF) under nitrogen was added methyl α-[3-(trifluoromethyl)benzylamino]-indole-3acetate (752 mg, 2.0 mmol) dissolved in 2 mL DMF. Stirring was continued at room temperature for 10 minutes. At the end of this time, 0.322 g (2.0 mmol) of parachlorobenzyl chloride was added and the reaction stirred at room temperature for one hour. The reaction was diluted with ether and the ether solution was washed two times with water. The ether extract was then washed with saturated brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give the crude product. Flash chromatography of the crude product with 100 g of silica gel and using hexane-ethyl acetate (4:10) as the eluent afforded 419 mg of the title compound.

Workup

  1. stirringthe reaction stirred at room temperature for one hour
  2. washthe ether solution was washed two times with water
  3. extractionThe ether extract
  4. washwas then washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give the crude product

Sources & evidence

ORD record
ord-3f8581bc16ea4d41a3c766acc9b0ade0
Source dataset
uspto-grants-1993_09
Patent number
US05245046

Linked notes

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