三氟-1-（2-呋喃基）-1，3-丁二酮 → 3,5-dichloro-2-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine

HRID 453071笔记

反应方程式

HRID 453071 反应方程式
[F:1][C:2]([F:14])([F:13])[C:3](=O)[CH2:4][C:5]([C:7]1[O:8][CH:9]=[CH:10][CH:11]=1)=O.[Cl:15][C:16]1[C:17]([NH:23][NH2:24])=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=1>C(O)(=O)C>[Cl:15][C:16]1[C:17]([N:23]2[C:5]([C:7]3[O:8][CH:9]=[CH:10][CH:11]=3)=[CH:4][C:3]([C:2]([F:14])([F:13])[F:1])=[N:24]2)=[N:18][CH:19]=[C:20]([Cl:22])[CH:21]=1

参与物

4

反应物 2

HCID 67594三氟-1-（2-呋喃基）-1，3-丁二酮HCID 6009663,5-二氯-2-肼基吡啶

产物 1

HCID 669396863,5-dichloro-2-(5-(furan-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridine收率 61%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

To a 250 mL flask, 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione (5.50 g, 26.7 mmol), 3,5-dichloro-2-hydrazinylpyridine (4.75 g, 26.7 mmol) and glacial acetic acid (100 mL) were added. The reaction mixture was heated to reflux. When the reaction completed, the reaction mixture was concentrated by rotary evaporator. Then ethyl acetate (300 mL) and water (150 mL) was added, the organic extracts were washed with saturated sodium bicarbonate solution (150 mL) and brine (150 mL) in sequence, dried over anhydrous magnesium sulfate and concentrated by rotary evaporator. The residue was purified by silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1/5) to give the product (5.66 g) as a yellow oil in 61% yield. 1H NMR (300 MHz, CDCl3): 8.514 (d, 1H), 7.974 (d, 1H), 7.362 (d, 1H), 6.917 (s, 1H), 6.388 (dd, 1H), 6.148 (d, 1H).

后处理

  1. temperatureThe reaction mixture was heated to reflux
  2. concentrationthe reaction mixture was concentrated by rotary evaporator
  3. additionThen ethyl acetate (300 mL) and water (150 mL) was added
  4. washthe organic extracts were washed with saturated sodium bicarbonate solution (150 mL) and brine (150 mL) in sequence
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated by rotary evaporator
  7. customThe residue was purified by silica gel column chromatography (Fluent: ethyl acetate/petroleum ether=1/5)

来源与证据

ORD记录
ord-d8074549ef634c59aad5111feb4bc17c
来源数据集
uspto-grants-2013_07
专利号
US08492409B2

反应笔记

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