Dimethylformamide → 1-(3-fluoro-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3,5-dimethyl pyridin-2(1H)-one

HRID 56076Notes

Reaction equation

HRID 56076 reaction equation
[CH3:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:10][C:11]1[CH:24]=[C:23](I)[CH:22]=[CH:21][C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C>[Cu]I.C(Cl)Cl.O>[F:10][C:11]1[CH:24]=[C:23]([N:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]2=[O:9])[CH:22]=[CH:21][C:12]=1[CH2:13][N:14]1[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 123485383,5-Dimethyl-1,2-dihydropyridin-2-oneHCID 900224931-(2-Fluoro-4-iodobenzyl)-4-methylpiperazine

Product 1

HCID 900226041-(3-fluoro-4-((4-methylpiperazin-1-yl)methyl)phenyl)-3,5-dimethyl pyridin-2(1H)-oneYield 37.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,5-dimethylpyridin-2(1H)-one (0.07 g, 0.57 mmol), 1-(2-fluoro-4-iodobenzyl)-4-methylpiperazine (0.19 g, 0.57 mmol), K2CO3 (0.08 g, 0.58 mmol), CuI (0.005 g, 0.026 mmol) and DMF (1 mL) was refluxed under N2. The reaction process was monitored by TLC. After the reaction was completed, the mixture was cooled to rt. To the resulting mixture was added H2O (5 mL) and CH2Cl2 (10 mL×3). The organic phase was separated, dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1) to give the title compound as a pale yellow solid (0.07 g, 37%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperaturewas refluxed under N2
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=1:1)

Sources & evidence

ORD record
ord-3427f3e07fab4469b603e83eefda3faa
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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