Ethyl Acetate → Ethyl 1-(3-trifluoromethylbenzyl)-1H-indole-2-carboxylate

HRID 505626Notes

Reaction equation

HRID 505626 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O>[F:15][C:16]([F:25])([F:26])[C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 73125Ethyl indole-2-carboxylateHCID 1230611-(Bromomethyl)-3-(trifluoromethyl)benzene

Product 1

HCID 68696914Ethyl 1-(3-trifluoromethylbenzyl)-1H-indole-2-carboxylateYield 88.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.492 g (2.6 mmol) of ethyl 1H-indole-2-carboxylate, of 0.683 g (2.86 mmol) of 3-trifluoromethylbenzyl bromide and of 0.898 g (6.5 mmol) of potassium carbonate in 50 ml of dimethylformamide is stirred at 60° C. for 24 hours. The reaction mixture is cooled and is poured into a mixture of ice-cold water and of ethyl acetate. After settling, the organic phase is separated and is then washed with two times 50 ml of water and then with 50 ml of a saturated sodium chloride solution. The solution is dried over magnesium sulfate and filtered, and then the filtrate is concentrated under reduced pressure. 0.8 g of an oil is obtained, which oil is used as is in the following stage.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe organic phase is separated
  3. washis then washed with two times 50 ml of water
  4. dry with materialThe solution is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-16dead8cdaf647ce826ca743bd76c58b
Source dataset
uspto-grants-2010_08
Patent number
US07781477B2

Reaction notes

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