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

HRID 626701
ノート
印刷プレビュー

反応式

HRID 626701 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4532c6d355074943a6863d25634fa6b1
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309240B2

反応ノート

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