2-Bromonaphthalene → 1-(4-Methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one

HRID 80039

Reaction equation

HRID 80039 reaction equation
N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]1[CH2:26][CH2:25][NH:24][C:23]1=[O:27].Br[C:29]1[CH:38]=[CH:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[CH3:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][C:17]=1[N:22]1[CH2:26][CH2:25][N:24]([C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[C:23]1=[O:27]

Participants

9

Reactant 4

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 596361701-(4-Methylpyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498718661-(4-Methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-oneYield 73%

Reagents, catalysts & solvents 4

HCID 83717Copper iodideCatalystHCID 887MethanolSolventHCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

Copper iodide (21.5 mg, 0.113 mmol), trans-1,2-diamino cyclohexane (0.041 mL, 0.339 mmol) and potassium carbonate (313 mg, 2.26 mmol) were added to 1,4-Dioxane (15 mL) previously sparged with argon (10 minutes). The reaction mixture was sparged with argon for a further 10 minutes, followed by the addition of 1-(4-methyl-pyridin-3-yl)-imidazolidin-2-one (I-14b: 200 mg, 1.13 mmol) and 2-bromo naphthalene (234 mg, 1.13 mmol). The resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (10% MeOH in chloroform). The reaction mixture was filtered through a celite and the bed was washed with chloroform. The organic layer was dried over Na2SO4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 1% MeOH in chloroform as eluent) afforded 250 mg (73% yield) of 1-(4-methyl-pyridin-3-yl)-3-naphthalen-2-yl-imidazolidin-2-one.

Workup

  1. custompreviously sparged with argon (10 minutes)
  2. customThe reaction mixture was sparged with argon for a further 10 minutes
  3. temperatureThe resulting mixture was heated
  4. filtrationThe reaction mixture was filtered through a celite
  5. washthe bed was washed with chloroform
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated
  8. customPurification by column chromatography (using silica gel of mesh size of 60-120, 1% MeOH in chloroform as eluent)

Sources & evidence

ORD record
ord-4c37a5aae42d4d56a69f1a90baaabf45
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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