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Phenylacetylene → 6,7-Dichloro-2,3-dimethoxy-5-(2-phenylethynyl)quinoxaline

HRID 842687
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HRID 842687 반응식
[Cl:1][C:2]1[C:3](I)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2.[C:18]1([C:24]#[CH:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[C:3]([C:25]#[C:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:4]2[C:9](=[CH:10][C:11]=1[Cl:12])[N:8]=[C:7]([O:13][CH3:14])[C:6]([O:15][CH3:16])=[N:5]2
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참가 물질

6

반응물 2

HCID 10821PhenylacetyleneHCID 106914616,7-Dichloro-2,3-dimethoxy-5-iodoquinoxaline

생성물 1

HCID 226148926,7-Dichloro-2,3-dimethoxy-5-(2-phenylethynyl)quinoxaline수율 77.1%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물
촉매
HCID 8471Triethylamine용매

실험 절차

A mixture of 6,7-dichloro-2,3-dimethoxy-5-iodoquinoxaline (Preparation 108, 5.0 g, 13 mmol), phenylacetylene (3.98 g, 39 mmol), bis(triphenylphosphine)palladium(II) chloride (0.913 g, 1.3 mmol) and copper(I) iodide (0.248 g, 1.3 mmol) in triethylamine (100 mL) was heated under reflux for 4 hours. After being cooled, the mixture was concentrated under reduced pressure and the residue partitioned between dichloromethane (200 mL) and brine (200 mL). The phases were separated and the aqueous phase extracted with dichloromethane (2×100 mL). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using hexane:dichloromethane (1:0 changing to 1:1, by volume) to afford 6,7-dichloro-2,3-dimethoxy-5-(2-phenylethynyl)quinoxaline (3.60 g, 77%) as a yellow solid, mp 170-172° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter being cooled
  4. concentrationthe mixture was concentrated under reduced pressure
  5. customthe residue partitioned between dichloromethane (200 mL) and brine (200 mL)
  6. customThe phases were separated
  7. extractionthe aqueous phase extracted with dichloromethane (2×100 mL)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by flash chromatography on silica gel, by gradient elution

출처 및 근거

ORD 기록
ord-425d72f438e14f929bb299420858b8d6
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06376490B1

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