Salicylaldehyde oxime → HCID 86710569, 화합물

HRID 1027176노트

반응식

HRID 1027176 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 86710569HCID 86710569, 화합물수율 19.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

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+].)

후처리

  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)

출처 및 근거

ORD 기록
ord-c9fd3502863a4db9b4f9aab4cc974de2
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729263B2

반응 노트

불러오는 중…