Phosphorus oxychloride → 4-Chloro-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine

HRID 626766노트

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HRID 626766 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Cl:11])[C:3]=1[N:12]1[CH:22]=[C:15]2[CH:16]=[N+:17]([O-])[CH:18]=[C:19]([F:20])[C:14]2=[N:13]1.P(Cl)(Cl)([Cl:25])=O>ClCCCl>[Cl:25][C:16]1[C:15]2=[CH:22][N:12]([C:3]3[C:2]([Cl:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][C:4]=3[Cl:11])[N:13]=[C:14]2[C:19]([F:20])=[CH:18][N:17]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 696716022-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5-oxide

생성물 1

HCID 866970684-Chloro-2-(2,6-dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine수율 40.2%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
70 °C

실험 절차

2-(2,6-Dichloro-4-nitrophenyl)-7-fluoro-2H-pyrazolo[4,3-c]pyridine 5-oxide (4.20 g, 12.24 mmol) was suspended in DCE (60 mL), under an atmosphere of nitrogen and phosphorus oxychloride (3.61 mL, 39.2 mmol) was added. The reaction mixture was heated at 70° C. for 95 minutes. The resultant mixture was cooled to room temperature and was carefully quenched by the addition of 10% aqueous sodium carbonate solution. The layers were separated and the aqueous layer was extracted with DCM (×4). The combined organic layers were filtered to remove insoluble solids, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane) to afford the title compound as a pale yellow solid (1.78 g, 40% yield). 1H NMR (300 MHz, CDCl3): δ 8.43 (s, 2H), 8.37 (d, J=2.2 Hz, 1H), 8.03 (d, J=3.0 Hz, 1H).

후처리

  1. customwas carefully quenched by the addition of 10% aqueous sodium carbonate solution
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (×4)
  4. filtrationThe combined organic layers were filtered
  5. customto remove insoluble solids
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography (0-50% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-f61855f85da547ceacd134b6048fb4a0
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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