N,N'-Dimethylethylenediamine → 3-Indol-1-yl-4-trifluoromethyl-benzoic Acid Methyl Ester

HRID 1918371Notes

Reaction equation

HRID 1918371 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[C:6]([NH2:14])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].CNCCNC.Br[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH:35]=[CH:36]Br>[Cu]I.CC(=O)OCC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[C:6]([N:14]2[C:31]3[C:30](=[CH:29][CH:34]=[CH:33][CH:32]=3)[CH:35]=[CH:36]2)[CH:5]=1

Participants

8

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 3639340o-Bromo-(2-bromo)vinylbenzeneHCID 15109485Methyl 3-amino-4-(trifluoromethyl)benzoate

Product 1

HCID 671729313-Indol-1-yl-4-trifluoromethyl-benzoic Acid Methyl EsterYield 44%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

690 mg of 3-Amino-4-trifluoromethyl-benzoic acid methyl ester, 650 mg of K2CO3, 30 mg of CuI, and 28 mg of N,N′-dimethylethylendiamine were suspended using 4.1 ml of anhydrous toluene. 410 mg of o-bromo-(2-bromo)vinylbenzene were added and the reaction mixture stirred at 110° C. for 14 h. The reaction mixture was allowed to cool to room temperature, 50 ml of EA added, filtrated, and evaporated. Chromatography on silica gel using EA/HEP (gradient) yielded 220 mg of the title compound, viscous oil.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltrated
  3. customevaporated

Sources & evidence

ORD record
ord-836ddda71d114190af2e73097deb94ef
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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