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

HRID 626675노트

반응식

HRID 626675 반응식
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N:20]1[CH:28]=[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:22]2=[N:21]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[N:20]1[CH:28]=[C:23]2[CH:24]=[N+:25]([O-:9])[CH:26]=[CH:27][C:22]2=[N:21]1

참가 물질

5

반응물 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 696716312-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 696711682-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

mCPBA (2.38 g, 13.88 mmol) was added to a cooled 0° C.) solution of 2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (2.27 g, 9.2 mmol) in DCM (55 mL) under nitrogen. The reaction was stirred for 3 hours, warmed to room temperature, and stirred for an additional 2 hours. Sodium thiosulfate (sat. aq.) was added and the layers were partitioned. The organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (5-10% methanol in DCM) to afford the title compound as a beige solid (2.13 g, 88% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.90 (dd, J=1.8, 0.9 Hz, 1H), 8.87 (s, 1H), 7.95 (dd, J=7.5, 1.8 Hz, 1H), 7.83 (dt, J=7.5, 1.0 Hz, 1H), 7.74 (td, J=8.3, 5.8 Hz, 1H), 7.65-7.63 (m, 2H).

후처리

  1. stirringstirred for an additional 2 hours
  2. customthe layers were partitioned
  3. washThe organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (5-10% methanol in DCM)

출처 및 근거

ORD 기록
ord-17f6105aa20d49019d78817ec19a685f
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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