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

HRID 2099505

反応式

HRID 2099505 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
145 °C

実験手順

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)+

後処理

  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)

出典と根拠

ORDレコード
ord-674d8f7f59364e6696a3ecbb50ab5572
出典データセット
uspto-grants-2009_08
特許番号
US07569592B2

関連ノート

読み込み中…