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

HRID 80023

反応式

HRID 80023 の反応式
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]

参加物

9

反応物 4

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

生成物 1

HCID 498729331-Naphthalen-2-yl-3-pyridin-3-ylimidazolidin-2-one収率 28%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 887Methanol溶媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-cc3974a47dfa4173aef581467474faa8
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

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