1,10-Phenanthroline → N-(4-Pyrazol-1-yl-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

HRID 655865ノート

反応式

HRID 655865 の反応式
N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1.[C:33]([O:37][C:38]([NH:40][NH2:41])=[O:39])([CH3:36])([CH3:35])[CH3:34]>[Cu](I)I.CN(C=O)C>[C:33]([O:37][C:38]([N:40]([C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:32]=[CH:31][CH:30]=[N:29]2)=[CH:24][CH:23]=1)[NH2:41])=[O:39])([CH3:36])([CH3:35])[CH3:34]

参加物

7

反応物 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 70091tert-Butyl carbazateHCID 27764811-(4-Iodophenyl)-1H-Pyrazole

生成物 1

HCID 68820898N-(4-Pyrazol-1-yl-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester収率 82.8%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Copper iodide (18 mg, 0.05 eq, 0.09 mmol), 1,10-phenanthroline (67 mg, 0.2 eq, 0.37 mmol) and caesium carbonate (0.84 g, 1.4 eq, 2.6 mmol) were mixed in a RB flask, placed under vacuum and purged with N2 (g). 1-(4-Iodo-phenyl)-1H-pyrazole (0.5 g, 1.0 eq, 1.85 mmol), hydrazine carboxylic acid tert-butyl ester (0.3 g, 1.2 eq, 2.22 mmol) and DMF (25 ml) were added to the mixture which was then heated to 80° C. with stirring under an inert atmosphere for 21 hours. The reaction mixture was allowed to cool and was then filtered through a silica pad, which was then washed with ethyl acetate. The filtrate was then concentrated to dryness in vacuo. The resultant residue was purified by column chromatography using heptane/ethyl acetate (3:1) as eluent to yield impure title compound (0.42 g). LCMS: [M+H]+=275, rt=1.25 min, 48% purity.

後処理

  1. custompurged with N2 (g)
  2. temperatureto cool
  3. filtrationwas then filtered through a silica pad, which
  4. washwas then washed with ethyl acetate
  5. concentrationThe filtrate was then concentrated to dryness in vacuo
  6. customThe resultant residue was purified by column chromatography

出典と根拠

ORDレコード
ord-a6c1ae55b6d94996b6b07f9a0070461f
出典データセット
uspto-grants-2011_12
特許番号
US08071607B2

反応ノート

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