2-Bromonaphthalene → 1-Naphthalen-2-yl-3-pyridin-3-ylimidazolidin-2-one

HRID 80023

Reaction equation

HRID 80023 reaction equation
N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].[N:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[CH2:25][CH2:24][NH:23][C:22]2=[O:26])[CH:16]=1.Br[C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=1>C(Cl)(Cl)Cl.[Cu](I)I.CO.O1CCOCC1>[CH:34]1[C:35]2[C:30](=[CH:29][CH:28]=[CH:37][CH:36]=2)[CH:31]=[CH:32][C:33]=1[N:23]1[CH2:24][CH2:25][N:21]([C:17]2[CH:16]=[N:15][CH:20]=[CH:19][CH:18]=2)[C:22]1=[O:26]

Participants

9

Reactant 4

HCID 113722-BromonaphthaleneHCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 148342041-(Pyridin-3-yl)imidazolidin-2-one

Product 1

HCID 498729331-Naphthalen-2-yl-3-pyridin-3-ylimidazolidin-2-oneYield 28%

Reagents, catalysts & solvents 4

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

Conditions

Temperature
110 °C

Procedure

Copper iodide (10.0 mg, 0.113 mmol), trans-1,2-diamino cyclohexane (10.0 mg, 0.091 mmol) and potassium carbonate (169 mg, 1.22 mmol) were added to a solution of 1,4-dioxane (5 mL) previously purged with argon (10 minutes). The reaction mixture was purged with argon for 10 minutes, followed by the addition of 1-pyridin-3-yl-imidazolidin-2-one (I-1b: 100 mg, 0.61 mmol) and 2-bromo naphthalene (126 mg, 0.61 mmol). The reaction 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 bed and the bed was washed with chloroform. The organic layer was concentrated and purification by column chromatography (using silica gel of mesh size of 60-120, 20% ethyl acetate in hexane as eluent) afforded 48 mg (28% yield) of 1-naphthalen-2-yl-3-pyridin-3-yl-imidazolidin-2-one.

Workup

  1. custompreviously purged with argon (10 minutes)
  2. customThe reaction mixture was purged with argon for 10 minutes
  3. temperatureThe reaction mixture was heated
  4. filtrationThe reaction mixture was filtered through a celite bed
  5. washthe bed was washed with chloroform
  6. concentrationThe organic layer was concentrated
  7. custompurification by column chromatography (using silica gel of mesh size of 60-120, 20% ethyl acetate in hexane as eluent)

Sources & evidence

ORD record
ord-cc3974a47dfa4173aef581467474faa8
Source dataset
uspto-grants-2014_09
Patent number
USRE045173E1

Linked notes

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