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Sodium Thiosulfate → 2-(2,6-Dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide

HRID 626701
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HRID 626701 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:18]=[C:13]2[CH:14]=[N:15][CH:16]=[CH:17][C:12]2=[N:11]1.C1C=C(Cl)C=C(C(OO)=[O:27])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[CH:18]=[C:13]2[CH:14]=[N+:15]([O-:27])[CH:16]=[CH:17][C:12]2=[N:11]1
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참가 물질

5

반응물 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 696716762-(2,6-dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 696710862-(2,6-Dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine-5-oxide수율 83%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a cooled (0° C.) solution of 2-(2,6-dichloro-4-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (1.6 g, 5.67 mmol) in DCM (30 mL) under nitrogen, was added mCPBA (1.47 g, 8.51 mmol). The reaction mixture was stirred at 0° C. for 2 hours, warmed to room temperature, and stirred for a further 16 hours. Sodium thiosulfate (sat. aq.) was added and the organic layer was separated, washed with sodium hydrogen carbonate (sat. aq.) and brine, dried over anhydrous magnesium sulfate, and concentrated to dryness under reduced pressure. The residue was purified by silica gel flash chromatography (5-10% methanol in DCM) to afford the title compound as a white solid (1.4 g, 83% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.90 (s, 1H), 8.82 (s, 1H), 7.98-7.87 (m, 3H), 7.83 (d, J=7.5 Hz, 1H).

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred for a further 16 hours
  3. customthe organic layer was separated
  4. washwashed with sodium hydrogen carbonate (sat. aq.) and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (5-10% methanol in DCM)

출처 및 근거

ORD 기록
ord-4532c6d355074943a6863d25634fa6b1
출처 데이터셋
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09309240B2

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