Reacción #5707

Ecuación de reacción

hexane ethyl acetate

parachlorobenzyl chloride

sodium hydride

methyl α-[3-(trifluoromethyl)benzylamino]-indole-3acetate

→

title compound

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

Disolventes

DMF

ether

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe reaction stirred at room temperature for one hour
2. 2
   Lavadothe ether solution was washed two times with water
3. 3
   ExtracciónThe ether extract
4. 4
   Lavadowas then washed with saturated brine
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otroto give the crude product

Procedimiento

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.

Fuente