m-Chloroperbenzoic acid → 2-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide

HRID 626794ノート

反応式

HRID 626794 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N:14][CH:15]=[C:16]([F:17])[C:11]2=[N:10]1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N+:14]([O-:27])[CH:15]=[C:16]([F:17])[C:11]2=[N:10]1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 696713422-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 677014502-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide収率 68.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

2-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine (9.95 g, 37.5 mmol) was suspended in DCM (150 mL) at 0° C. and meta-chloroperbenzoic acid (12.9 g, 75 mmol) was added. The reaction mixture was stirred at 0° C. for 2 hours then allowed to reach room temperature and stirred for another 3 hours. The resultant mixture was quenched with saturated aqueous sodium thiosulfate solution and the layers were separated. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether and the solid obtained was filtered off and dried to afford the title compound as a white solid (7.22 g, 68% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.04 (d, J=2.6 Hz, 1H), 8.88 (d, J=1.4 Hz, 1H), 8.35 (dd, J=6.4, 1.5 Hz, 1H), 7.82-7.73 (m, 1H), 7.72-7.62 (m, 2H).

後処理

  1. customto reach room temperature
  2. stirringstirred for another 3 hours
  3. customThe resultant mixture was quenched with saturated aqueous sodium thiosulfate solution
  4. customthe layers were separated
  5. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was triturated with diethyl ether
  10. customthe solid obtained
  11. filtrationwas filtered off
  12. customdried

出典と根拠

ORDレコード
ord-5be0a2739af841b69d530ffda6f7bd0a
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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