3-(Trifluoromethyl)aniline → HCID 90311569, compound

HRID 927207Notes

Reaction equation

HRID 927207 reaction equation
C(O[C:9]1[CH2:13][CH:12]([CH3:14])[C:11](=[O:15])[CH:10]=1)C1C=CC=CC=1.[H][H].[F:18][C:19]([F:28])([F:27])[C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23].FC(F)(F)S([O-])(=O)=O.[Yb+3].FC(F)(F)S([O-])(=O)=O.FC(F)(F)S([O-])(=O)=O>[Pd].C1(C)C=CC=CC=1.ClCCl.O>[CH3:14][CH:12]1[C:11](=[O:15])[CH:10]=[C:9]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:20]([C:19]([F:18])([F:27])[F:28])[CH:21]=2)[CH2:13]1

Participants

9

Reactant 4

HCID 73753-(Trifluoromethyl)aniline2×HCID 2733225Ytterbium triflateHCID 90310884HCID 90310884, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 90311569HCID 90311569, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(benzyloxy)-5-methylcyclopent-2-enone (intermediate 22, 210 mg, 1.04 mmol) and Palladium on carbon (10%, 127 mg) in toluene (3.0 mL) is treated with hydrogen (3.4 bar) for 9 h. The mixture is filtered, and the filtrate is treated with 3-(tri-fluormethyl)aniline (130 μL, 1.04 mmol) and Ytterbium(III) trifluormethanesulfonate (3 mg, 5 μmol) and stirred at room temperature over night. Another portion of 3-(trifluor-methyl)aniline (65 μL, 0.52 mmol) is added, and the mixture is stirred over night. Water and dichloromethane is added, and the phases are separated. The organic phase is concentrated under reduced pressure, and the residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 136 mg; ESI mass spectrum [M+H]+=256; Retention time HPLC: 0.55 min (X012_S01).

Workup

  1. filtrationThe mixture is filtered
  2. stirringthe mixture is stirred over night
  3. customthe phases are separated
  4. concentrationThe organic phase is concentrated under reduced pressure
  5. customthe residue is purified by reversed phase HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% TFA)
  6. custom0.55 min (X012_S01)

Sources & evidence

ORD record
ord-edf31daf963f4b129430abc26e524ff3
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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