Piperidine → 6-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

HRID 2112821Notes

Reaction equation

HRID 2112821 reaction equation
I[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:12]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]1)[CH:6]=[C:5]2[CH3:19].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:28]=[CH:29][C:30]([C:33]#[CH:34])=[N:31][CH:32]=2)=[CH:23][CH:22]=1.N1CCCCC1.CCOC(C)=O>O1CCOCC1.[Cu]I>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:28]=[CH:29][C:30]([C:33]#[C:34][C:2]3[CH:3]=[C:4]4[C:9](=[CH:10][CH:11]=3)[N:8]=[C:7]([N:12]3[CH2:17][CH2:16][CH:15]([CH3:18])[CH2:14][CH2:13]3)[CH:6]=[C:5]4[CH3:19])=[N:31][CH:32]=2)=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 578453285-(4-Chloro-phenyl)-2-ethynyl-pyridineHCID 690607816-Iodo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

Product 1

HCID 576433036-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methyl-2-(4-methylpiperidin-1-yl)quinoline

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution of 293 mg (0.8 mmol) of 6-iodo-4-methyl-2-(4-methylpiperidin-1-yl)quinoline, 184 mg (0.8 mmol, 93% purity) 5-(4-chlorophenyl)-2-ethynylpyridine, and 158 μL (1.6 mmol) of piperidine in 4 mL of 1,4-dioxane is evacuated three times and gassed with argon. After the addition of 3 mg (0.016 mmol) of CuI and 13 mg (0.016 mmol) of PdCl2(dppf)-DCM complex, the reaction mixture is stirred for 4 hours at RT. It is combined with 10 mL of EtOAc, and the precipitate is filtered off, washed with a little EtOAc and MeOH, and dried in the air. Yield: 240 mg (66% of theoretical); C29H26ClN3 (M=451.990); calc.: molpeak (M+H)+: 452/454 (Cl); found: molpeak (M+H)+: 452/454 (Cl); HPLC-MS: 6.1 min (method B).

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with a little EtOAc and MeOH
  3. customdried in the air
  4. custom6.1 min (method B)

Sources & evidence

ORD record
ord-037f7b450e3843c99f8bd8570a3841ce
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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