Water → 2-[1-(3-chlorophenyl)-1H-pyrazol-3-yl]pyridine

HRID 2099505

반응식

HRID 2099505 반응식
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:2]1.F[C:13]1[CH:14]=[C:15]([Cl:19])[CH:16]=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[Cl:19][C:15]1[CH:14]=[C:13]([N:1]2[CH:5]=[CH:4][C:3]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=3)=[N:2]2)[CH:18]=[CH:17][CH:16]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2230871-Chloro-3-fluorobenzeneHCID 27976572-(1H-Pyrazol-3-Yl)Pyridine

생성물 1

HCID 101492372-[1-(3-chlorophenyl)-1H-pyrazol-3-yl]pyridine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
145 °C

실험 절차

2-(1H-Pyrazol-3-yl)pyridine (435 mg, 3 mmol), 3-fluoro-1-chlorobenzene (0.32 mL, 3 mmol) and K2CO3 (830 mg, 6 mmol) were dissolved in DMF (10 mL) under Ar (g) and heated at 145° C. for 18 h. After cooling to ambient temperature, H2O (40 mL) and EtOAc (40 mL) were added and the reaction mixture shaken, the EtOAc layer was separated and the aqueous layer shaken with EtOAc (2×30 mL). The combined organic layers were washed with brine (3×40 mL), dried over Na2SO4 and concentrated onto silica gel. The crude material was purified by liquid chromatography on silica gel, eluting with EtOAc:hexane (1:1) to afford 2-[1-(3-chlorophenyl)-1H-pyrazol-3-yl]pyridine as as solid. 1H NMR (CD3Cl, 300 MHz) δ 8.68-8.69 (1H, m), 8.13-8.16 (1H, m), 8.01 (1H, m), 7.88 (11H, m), 7.79 (1H, ddd), 7.66-7.68 (1H, m), 7.42 (1H, dd), 7.26-7.31 (2H, m), 7.16 (1H, d). MS (ESI) 256 (M+H)+

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customthe EtOAc layer was separated
  3. stirringthe aqueous layer shaken with EtOAc (2×30 mL)
  4. washThe combined organic layers were washed with brine (3×40 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated onto silica gel
  7. customThe crude material was purified by liquid chromatography on silica gel
  8. washeluting with EtOAc:hexane (1:1)

출처 및 근거

ORD 기록
ord-674d8f7f59364e6696a3ecbb50ab5572
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569592B2

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