Piperidine → 3-Benzyl-4-(3-Phenylethynyl-Phenyl)-8-Trifluoromethyl-Quinoline

HRID 2104795Notes

Reaction equation

HRID 2104795 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[CH:25])[CH:19]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:26]([F:29])([F:28])[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1CCCCC1>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]#[C:25][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:19]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:26]([F:29])([F:28])[F:27])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 8082PiperidineHCID 11575IodobenzeneHCID 86055589HCID 86055589, compound

Product 1

HCID 669139163-Benzyl-4-(3-Phenylethynyl-Phenyl)-8-Trifluoromethyl-QuinolineYield 77.7%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 3-benzyl-4-(3-ethynyl-phenyl)-8-trifluoromethyl-quinoline (80 mg, 0.2 mmol), iodobenzene 84 mg, 0.4 mmol), piperidine (80 mg, 0.9 mmol) in toluene (2.0 mL) is treated with Pd(Cl)2(PPh3)2 (8.0 mg) and heated at 90° C. for 3 h. The reaction is then cooled and concentrated in vacuo. The residue is taken up in ethyl acetate and washed with 10 mL (1N HCl). The organic layer is dried and concentrated in vacuo to provide after chromatography 72 mg (75%) of the title compound. MS (ES) m/z 464.1.

Workup

  1. temperatureThe reaction is then cooled
  2. concentrationconcentrated in vacuo
  3. washwashed with 10 mL (1N HCl)
  4. customThe organic layer is dried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a255bf1320a843a399a55e4b987b25eb
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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