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

HRID 432619ノート

反応式

HRID 432619 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 241Benzene溶媒

反応条件

温度
60 °C

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-b3638a0bd3904b26a3442cfa33b7aabb
出典データセット
uspto-grants-2003_12
特許番号
US06664256B1

反応ノート

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