Ethyl chloroformate → Ethyl alpha-[3(trifluoromethyl)-benzylamino]-1-ethoxycarbonyl-indole-3-acetate hydrochloride

HRID 5606Notes

Reaction equation

HRID 5606 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][CH:8]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[H-].[Na+].[Cl:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>CN(C=O)C>[ClH:30].[F:27][C:2]([F:1])([F:26])[C:3]1[CH:4]=[C:5]([CH:23]=[CH:24][CH:25]=1)[CH2:6][NH:7][CH:8]([C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:15]=1)[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 19796625HCID 19796625, compound

Product 1

HCID 19796595Ethyl alpha-[3(trifluoromethyl)-benzylamino]-1-ethoxycarbonyl-indole-3-acetate hydrochlorideYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. stirringStirring
  2. waitwas continued for two hours at room temperature
  3. customAt the end of this time, the reaction contents
  4. extractionthe aqueous solution extracted with ether
  5. washthe ether solution washed with saturated brine
  6. dry with materialdried over anhydrous Na2SO4
  7. customRemoval of the solvent in vacuo
  8. customgave the crude product which
  9. customwas chromatographed with 80 g of silica gel

Sources & evidence

ORD record
ord-37e9705164da464eb5088a85a9aeda49
Source dataset
uspto-grants-1993_09
Patent number
US05245046

Reaction notes

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