Salicylaldehyde oxime → (1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-yl)methanol

HRID 1027171노트

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HRID 1027171 반응식
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][NH:6][CH:7]=1.C(=NO)C1C(=CC=CC=1)O.C(=O)([O-])[O-].[Cs+].[Cs+].I[C:25]1[C:26]([Br:33])=[C:27]([O:31][CH3:32])[CH:28]=[CH:29][CH:30]=1>CN(C)C=O>[Br:33][C:26]1[CH:25]=[CH:30][C:29]([N:5]2[CH:4]=[C:3]([CH2:2][OH:1])[CH:7]=[N:6]2)=[CH:28][C:27]=1[O:31][CH3:32]

참가 물질

6

반응물 4

HCID 7200Salicylaldehyde oximeHCID 10796Cesium carbonateHCID 30152104-HydroxymethylpyrazoleHCID 236362102-Bromo-3-iodoanisole

생성물 1

HCID 86710564(1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-yl)methanol수율 55.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

A mixture of 4-(hydroxymethyl)pyrazole (500 mg, 5.10 mmol), salicylaldoxime (140 mg, 1.019 mmol), cesium carbonate (4.98 g, 15.29 mmol), cuprous oxide (58.2 mg, 0.306 mmol), iodobromoanisole (1.59 g, 5.10 mmol) and N,N-dimethyl-formamide (10 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 reaction mixture was cooled to RT, then filtered through celite, and the filtrate was concentrated in vacuo. The crude material was purified by column chromotography (10% to 60% EtOAc in heptanes) to give (1-(4-bromo-3-methoxyphenyl)-1H-pyrazol-4-yl)methanol (800 mg, MS: 285.3 [M+H+].)

후처리

  1. customvial fitted with an N2 inlet and magnetic stir bar
  2. temperatureThe reaction mixture was cooled to RT
  3. filtrationfiltered through celite
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe crude material was purified by column chromotography (10% to 60% EtOAc in heptanes)

출처 및 근거

ORD 기록
ord-2e83621e5fee4a4e85f60d0c7bd8d5e1
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08729263B2

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