碳酸氢铯 → 3-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

HRID 404703

反应方程式

HRID 404703 反应方程式
[CH3:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1F>CN(C=O)C>[F:16][C:17]1[CH:18]=[C:19]([N+:24]([O-:26])=[O:25])[CH:20]=[CH:21][C:22]=1[O:8][C:7]1[C:2]([CH3:1])=[N:3][C:4]([CH3:9])=[CH:5][CH:6]=1

参与物

5

反应物 3

HCID 10796碳酸氢铯HCID 707322,6-二甲基-3-羟基吡啶2,6-二甲基-3-羟基吡啶HCID 1230533,4-二氟硝基苯

产物 1

HCID 592873193-(2-Fluoro-4-nitrophenoxy)-2,6-dimethyl-pyridine

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
140 °C

实验过程

2,6-Dimethyl-pyridin-3-ol (3.0 g, 24.35 mmol) and cesium carbonate (15.87 g, 48.71 mmol) were added to a solution of 3,4-difluoronitrobenzene (3.87 g, 24.35 mmol) in DMF (30 ml). The mixture was heated at 140° C. for 2 hours. After cooling to room temperature it was filtered through diatomaceous earth and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; 2% methanol/DCM as eluent) to yield intermediate D14 (5.88 g, 92%).

后处理

  1. temperatureAfter cooling to room temperature it
  2. filtrationwas filtered through diatomaceous earth
  3. customthe solvent evaporated in vacuo
  4. customThe crude product was purified by column chromatography (silica gel; 2% methanol/DCM as eluent)
  5. customto yield intermediate D14 (5.88 g, 92%)

来源与证据

ORD记录
ord-d4df6e9c113040a08a2f20ae8c1a501d
来源数据集
uspto-grants-2014_06
专利号
US08748621B2

关联笔记

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