Imidazole → methylphenylphosphinic acid 3-((E)-styryl)-1H-indazol-5-yl ester

HRID 1726052ノート

反応式

HRID 1726052 の反応式
[CH:1]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([OH:18])[CH:16]=2)[NH:11][N:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.N1C=CN=C1.[CH3:24][P:25](Cl)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:26].O>ClCCl>[CH:1](/[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][P:25]([CH3:24])([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[CH:16]=2)[NH:11][N:10]=1)=[CH:2]\[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 795Imidazole3 回HCID 962WaterHCID 21983Methyl(phenyl)phosphinoyl chloride3 回HCID 688387233-styryl-1H-indazol-5-ol

生成物 1

HCID 11428770methylphenylphosphinic acid 3-((E)-styryl)-1H-indazol-5-yl ester収率 28.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 20 mg of 3-styryl-1H-indazol-5-ol, 5.76 mg of imidazole and 20.7 mg of methylphenylphosphinic chloride in 5 ml of dichloromethane is stirred at ambient temperature. After stirring for approximately one hour, 5.76 mg of imidazole and 20.7 mg of methylphenylphosphinic chloride are added. The suspension is stirred at ambient temperature for approximately 18 hours. 10 mg of imidazole and 70 mg of methylphenylphosphinic chloride are added. After 30 hours at ambient temperature, the reaction medium is treated with 10 ml of distilled water. The aqueous phase is extracted with 2×10 ml of dichloromethane. The organic phase is dried over magnesium sulfate and concentrated under reduced pressure in a rotary evaporator. The reaction crude is purified by preparative LC/MS to obtain 9.1 mg of methylphenylphosphinic acid 3-((E)-styryl)-1H-indazol-5-yl ester.

後処理

  1. stirringThe suspension is stirred at ambient temperature for approximately 18 hours
  2. waitAfter 30 hours at ambient temperature
  3. extractionThe aqueous phase is extracted with 2×10 ml of dichloromethane
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure in a rotary evaporator
  6. customThe reaction crude
  7. customis purified by preparative LC/MS

出典と根拠

ORDレコード
ord-619dbf0ab4d84c8fac3c44929f522b7f
出典データセット
uspto-grants-2009_02
特許番号
US07491710B2

反応ノート

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