Ethyl Acetate → 4-Chloro-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

HRID 626676노트

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HRID 626676 반응식
[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-])[CH:15]=[CH:16][C:11]2=[N:10]1.C(OCC)(=O)C.C(=O)([O-])O.[Na+].P(Cl)(Cl)([Cl:32])=O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:32][C:13]1[C:12]2=[CH:18][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[CH:16]=[CH:15][N:14]=1

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 696711682-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide

생성물 1

HCID 866970434-Chloro-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine수율 27%

시약·촉매·용매 1

HCID 70681Tetrabutylammonium Chloride촉매

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온도
85 °C

실험 절차

2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine 5-oxide (2.13 g, 8.1 mmol) was added to a solution of tetrabutylammonium chloride (2.24 g, 8.1 mmol) in phosphorous oxychloride (16 mL) and the reaction mixture was heated at 85° C. for 5 hours. The reaction mixture was cooled to room temperature and poured into a mixture of ethyl acetate and sodium hydrogen carbonate (sat. aq.). The organic phase was separated, washed with sodium hydrogen carbonate (sat. aq.) and brine, dried over anhydrous sodium sulfate, 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 (606 mg, 27% yield). 1H NMR (400 MHz, CDCl3): δ 8.36 (s, 1H), 8.12 (d, J=6.3 Hz, 1H), 7.57 (d, J=6.5 Hz, 1H), 7.55-7.50 (m, 1H), 7.45 (d, J=8.3 Hz, 1H), 7.27 (m, 1H). LCMS (Method D): RT=3.29 min, m/z: 282 [M+H+].

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe organic phase was separated
  3. washwashed with sodium hydrogen carbonate (sat. aq.) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel flash chromatography (20% ethyl acetate in cyclohexane)

출처 및 근거

ORD 기록
ord-cb32466da680419d8593dbca86f1ab14
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309240B2

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