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

HRID 626675ノート

反応式

HRID 626675 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-17f6105aa20d49019d78817ec19a685f
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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