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

HRID 2216893

반응식

HRID 2216893 반응식
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

참가 물질

8

반응물 5

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 1443413-IodobenzonitrileHCID 5354370trans-DibenzylideneacetoneHCID 178420123HCID 178420123, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 7237O-Xylene용매

반응 조건

온도
120 °C

실험 절차

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 (0.20 g, 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.

후처리

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

출처 및 근거

ORD 기록
ord-899a4a96a3cf41e4a4fa6d93a65fb868
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112595B2

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