Phosphorus oxychloride → 4-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626659

반응식

HRID 626659 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH:18]=[C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[CH:16][C:11]2=[N:10]1.P(Cl)(Cl)([Cl:21])=O.C(=O)([O-])O.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Cl:21][C:13]1[C:12]2=[CH:18][N:9]([C:3]3[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=3[Cl:8])[N:10]=[C:11]2[CH:16]=[CH:15][N:14]=1

참가 물질

6

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 677015532-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide

생성물 1

HCID 866970364-chloro-2-(2,6-dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine수율 49%

시약·촉매·용매 2

HCID 70681Tetrabutylammonium Chloride촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

2-(2,6-Dichlorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide (1.12 g, 4 mmol) was slowly added to phosphorous oxychloride (8 mL). Tetrabutylammonium chloride (1.11 g, 4 mmol) was then added. The reaction mixture was heated at 80° C. for 5 hours and then cooled to room temperature. The reaction was poured into a mixture of ethyl acetate and sodium hydrogen carbonate (sat. aq.) and the layers were partitioned. The organic layer was washed with sodium hydrogen carbonate (sat. aq.) and brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resultant residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (590 mg, 49% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.33 (d, J=1.0 Hz, 1H), 8.11 (d, J=6.0 Hz, 1H), 7.83 (d, J=1.3 Hz, 1H), 7.82-7.81 (m, 1H), 7.75-7.71 (m, 1H). LCMS (Method D): RT=3.42 min, m/z: 298 [M+H+].

후처리

  1. temperaturecooled to room temperature
  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 sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-4dd650f0ed7046cb95d4f42a57c97827
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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