Sodium Carbonate → 4-Chloro-2-(2-chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626795노트

반응식

HRID 626795 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[N:9]1[CH:19]=[C:12]2[CH:13]=[N+:14]([O-])[CH:15]=[C:16]([F:17])[C:11]2=[N:10]1.P(Cl)(Cl)([Cl:22])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[Cl:22][C:13]1[C:12]2=[CH:19][N:9]([C:3]3[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[N:10]=[C:11]2[C:16]([F:17])=[CH:15][N:14]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 677014502-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide

생성물 1

HCID 866970804-Chloro-2-(2-chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine수율 40.1%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
70 °C

실험 절차

2-(2-Chloro-6-fluorophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5 oxide (7.2 g, 25.6 mmol) was suspended in DCE (130 mL) under an atmosphere of nitrogen and phosphorus oxychloride (7.2 mL, 77.0 mmol) was added. The reaction mixture was heated at 70° C. for 5 hours and then allowed to cool to room temperature. The resultant mixture was poured cautiously onto saturated aqueous sodium carbonate solution, with stirring, and the layers were separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane) to afford the title compound as a white solid (3.08 g, 40% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.54 (d, J=2.5 Hz, 1H), 8.22 (d, J=3.4 Hz, 1H), 7.86-7.78 (m, 1H), 7.76-7.66 (m, 2H).

후처리

  1. temperatureto cool to room temperature
  2. customthe layers were separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-6110e9b1c89c4d0bb2d7540204893a0c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

반응 노트

불러오는 중…