Reaction #5702

Reaction equation

ethyl chloroformate

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

sodium hydride

→

title compound

Yield 66.4%

Ethyl α-[3(trifluoromethyl)-benzylamino]-1-ethoxycarbonyl-indole-3-acetate hydrochloride

Yield 66.4%

Solvents

DMF

Conditions

Workup

1. 1
   workup.STIRRINGStirring
2. 2
   workup.WAITwas continued for two hours at room temperature
3. 3
   OtherAt the end of this time, the reaction contents
4. 4
   Extractionthe aqueous solution extracted with ether
5. 5
   Washthe ether solution washed with saturated brine
6. 6
   Dryingdried over anhydrous Na2SO4
7. 7
   OtherRemoval of the solvent in vacuo
8. 8
   Othergave the crude product which
9. 9
   Otherwas chromatographed with 80 g of silica gel

Procedure

To a magnetically stirred solution of ethyl α-[3(trifluoromethyl)-benzylamino]-indole-3-acetate (1.00 g, 2.66 mmol) in 15 mL of DMF was added under nitrogen 0.112 g (2.79 mmol) of sodium hydride (60% oil dispersion). After stirring at room temperature for 10 minutes, 0.26 ml (2.79 mmol) of ethyl chloroformate was added. Stirring was continued for two hours at room temperature. At the end of this time, the reaction contents were poured into ice water, the aqueous solution extracted with ether and the ether solution washed with saturated brine and dried over anhydrous Na2SO4. Removal of the solvent in vacuo gave the crude product which was chromatographed with 80 g of silica gel using hexane-ethyl acetate (4:1) to yield 0.857 g of the title compound.

Source