Salicylaldehyde oxime → HCID 86710569、化合物

HRID 1027176ノート

反応式

HRID 1027176 の反応式
Cl.Cl.[NH:3]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4]1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:25][C:26]1[CH:31]=[CH:30][C:29](I)=[CH:28][C:27]=1[O:33][CH3:34]>CN(C)C=O>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([N:3]2[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4]2)=[CH:28][C:27]=1[O:33][CH3:34]

参加物

6

反応物 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 121872021-Bromo-4-iodo-2-methoxybenzeneHCID 133489691H-Pyrazol-4-amine--hydrogen chloride (1/2)

生成物 1

HCID 86710569HCID 86710569、化合物収率 19.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

A mixture of pyrazole-4-amine dihydrochloride (0.75 g, 4.79 mmol), salicylaldoxime (0.131 g, 0.96 mmol), cesium carbonate (4.69 g, 14.38 mmol), cuprous oxide (0.06 g, 0.29 mmol), 1-bromo-4-iodo-2-methoxybenzene (1.5 g, 4.79 mmol) and N,N-dimethyl-formamide (5 mL) were combined in a microwave vial fitted with an N2 inlet and magnetic stir bar. The reaction mixture was stirred under a nitrogen atmosphere at 90° C. overnight. The solution obtained was allowed to cool to RT, then filtered through celite and the filtrate was concentrated in vacuo. The crude material was purified by silica gel chromotography (10% to 60% EtOAc in heptanes) to give 1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-amine (250 mg, MS: 270.2 [M+H+].)

後処理

  1. customvial fitted with an N2 inlet and magnetic stir bar
  2. customThe solution obtained
  3. temperatureto cool to RT
  4. filtrationfiltered through celite
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe crude material was purified by silica gel chromotography (10% to 60% EtOAc in heptanes)

出典と根拠

ORDレコード
ord-c9fd3502863a4db9b4f9aab4cc974de2
出典データセット
uspto-grants-2014_05
特許番号
US08729263B2

反応ノート

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