Potassium Carbonate → 1-Naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one

HRID 80105

反応式

HRID 80105 の反応式
N[C@@H]1CCCC[C@H]1N.C(=O)([O-])[O-].[K+].[K+].Br[C:16]1[CH:17]=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[N:36]1[CH2:40][CH2:39][NH:38][C:37]1=[O:41]>CCCCCC.[Cu](I)I.C(OCC)(=O)C.O1CCOCC1>[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][C:27]=1[N:36]1[CH2:40][CH2:39][N:38]([C:16]2[CH:17]=[N:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=2)[C:37]1=[O:41]

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 438061,2-Diaminocyclohexane, trans-HCID 111279913-Bromo-5-(trifluoromethyl)pyridineHCID 596361671-Naphthalen-2-yl-imidazolidin-2-one

生成物 1

HCID 596362161-Naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one収率 52%

試薬・触媒・溶媒 4

HCID 83717Copper iodide触媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

Copper iodide (12.6 mg, 0.066 mmol), trans-1,2-diamino cyclohexane (22.79 mg, 0.199 mmol) and potassium carbonate (183.5 mg, 1.32 mmol) were added to 1,4-dioxane (5 mL) and 3-bromo-5-trifluoromethyl-pyridine (150 mg, 0.66 mmol) previously degassed with argon (10 minutes). The reaction was purged with argon for a further 10 minutes, followed by the addition of 1-naphthalen-2-yl-imidazolidin-2-one (I-79b: 140 mg, 0.66 mmol) and the resulting mixture was heated to reflux at 110° C. for 15 hours. The reaction was monitored by TLC (50% ethyl acetate in hexane). The reaction mixture was filtered through celite and the bed was washed with chloroform. The organic layer was dried over Na2O4 and concentrated. Purification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant) afforded 120 mg (52% yield) of 1-naphthalen-2-yl-3-(5-trifluoromethyl-pyridin-3-yl)-imidazolidin-2-one.

後処理

  1. custompreviously degassed with argon (10 minutes)
  2. customThe reaction was purged with argon for a further 10 minutes
  3. temperaturethe resulting mixture was heated
  4. filtrationThe reaction mixture was filtered through celite
  5. washthe bed was washed with chloroform
  6. customThe organic layer was dried over Na2O4
  7. concentrationconcentrated
  8. customPurification by column chromatography (using silica gel of mesh size of 60-120, 30% EtOAc in hexane as eluant)

出典と根拠

ORDレコード
ord-b4701bd379cf4461a06ebbf58e991c9b
出典データセット
uspto-grants-2014_09
特許番号
USRE045173E1

関連ノート

読み込み中…