1,10-Phenanthroline → 3-(4-Pyridin-2-yl-imidazol-1-yl)-benzonitrile

HRID 432003

反応式

HRID 432003 の反応式
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=CC(/C=C/C1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]1[N:46]=[CH:47][NH:48][CH:49]=1.I[C:51]1[CH:52]=[C:53]([CH:56]=[CH:57][CH:58]=1)[C:54]#[N:55]>C1(C)C(C)=CC=CC=1.ClCCl>[N:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[C:45]1[N:46]=[CH:47][N:48]([C:51]2[CH:58]=[CH:57][CH:56]=[C:53]([C:54]#[N:55])[CH:52]=2)[CH:49]=1

参加物

8

反応物 5

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1443413-IodobenzonitrileHCID 5354370trans-DibenzylideneacetoneHCID 178420123HCID 178420123、化合物

生成物 1

HCID 112420363-(4-Pyridin-2-yl-imidazol-1-yl)-benzonitrile収率 8.3%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 7237O-Xylene溶媒

反応条件

温度
120 °C

実験手順

To a flame dried, argon purged screw-cap vial, containing copper (I) triflate.benzene complex (0.01 g, 0.03 mmol), 1,10-phenanthroline (0.10 g, 0.54 mmol), trans-dibenzylideneacetone (0.01 g, 0.03 mmol) and cesium carbonate (0.20g, 0.60 mmol) was added a solution of 4-(2-pyridyl)imidazole (0.08 g, 0.54 mmol) and 3-iodobenzonitrile (0.19 g, 0.82 mmol) in ortho-xylene (2 mL). The resulting brownish black reaction mixture was heated overnight at 120° C. After cooling, the reaction mixture was diluted with dichloromethane (20 mL) and washed sequentially with saturated ammonium chloride (20 mL) and brine (20 mL). The organic phase was then dried with sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography of the crude residue using 1% methanol (2 M in ammonia) in dichloromethane afforded 11 mg of 4-(2-pyridyl)-1-(3-cyanophenyl)-1H-imidazole, as an off-white solid.

後処理

  1. customTo a flame dried
  2. customargon purged
  3. customscrew-cap vial
  4. additioncontaining copper (I) triflate
  5. customThe resulting brownish black reaction mixture
  6. temperatureAfter cooling
  7. washwashed sequentially with saturated ammonium chloride (20 mL) and brine (20 mL)
  8. dry with materialThe organic phase was then dried with sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-16b5d23edf5a421c90fe9c73a295dcbc
出典データセット
uspto-grants-2003_12
特許番号
US06660753B2

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