3,4-Bis(4-methoxyphenyl)-6-chloropyridazine → 3,4-Bis(4-methoxyphenyl)-6-phenylpyridazine

HRID 432619

반응식

HRID 432619 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][C:12](Cl)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1.[C:24]1([Mg]Br)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.C(Cl)Cl>C1C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][C:12]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:13][C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 125680843,4-Bis(4-methoxyphenyl)-6-chloropyridazineHCID 21908982Water methylene chlorideHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 121138423,4-Bis(4-methoxyphenyl)-6-phenylpyridazine수율 36.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 241Benzene용매

반응 조건

온도
60 °C

실험 절차

3,4-Bis(4-methoxyphenyl)-6-chloropyridazine [Eur. J. Med. Chem.-Chimica Therapeutica, 14, 53-60 (1979)] (309.3 mg, 0.95 mmol) was dissolved in benzene (2 ml). Tetrakis(triphenylphosphine)palladium [Pd(Ph3P)4] (90.6 mg, 0.08 mmol) and phenylmagnesium bromide (1.0 M tetrahydrofuran solution) (1.5 ml) were then added successively, followed by stirring at 60° C. for 75 minutes. After water-methylene chloride was added to the reaction mixture, the mixture was extracted with methylene chloride and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off and the residue was then separated and purified by chromatography on a silica gel column [silica gel (40 g), hexane/ethyl acetate (2/1)], whereby the title compound was obtained as a pale yellow amorphous solid (129 mg, 36.9%)

후처리

  1. extractionthe mixture was extracted with methylene chloride
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off
  4. customthe residue was then separated
  5. custompurified by chromatography on a silica gel column [silica gel (40 g), hexane/ethyl acetate (2/1)], whereby the title compound

출처 및 근거

ORD 기록
ord-b3638a0bd3904b26a3442cfa33b7aabb
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664256B1

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