喹啉 → 4-[2-(4-Fluorophenyl)thiophen-3-yl]pyridine

HRID 9880

反应方程式

HRID 9880 反应方程式
N1C2C(=CC=CC=2)C=CC=1.C([C:14]1[S:18][C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:16]([C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)[CH:15]=1)(O)=O>[Cu]>[F:25][C:22]1[CH:21]=[CH:20][C:19]([C:17]2[S:18][CH:14]=[CH:15][C:16]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=2)=[CH:24][CH:23]=1

参与物

4

反应物 2

HCID 7047喹啉HCID 219885025-Carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene

产物 1

HCID 219884884-[2-(4-Fluorophenyl)thiophen-3-yl]pyridine收率 109.6%

试剂、催化剂与溶剂 1

HCID 23978铜催化剂

反应条件

温度
240 °C

实验过程

Quinoline (42 ml) and copper powder (2.95 g, 46.4 mmol) were added to 5-carboxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)thiophene (12.64 g (42.2 mmol), prepared as described in 2))), and the resulting mixture was stirred at 240° C. for 2.5 hours. At the end of this time, the reaction mixture was cooled to room temperature and was filtered off. The filtrate was partitioned between ethyl acetate and a saturated aqueous solution of ammonium chloride. The organic layer was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=1:1), to give the title compound (11.81 g) as a brown powder (yield quantitative).

后处理

  1. temperatureAt the end of this time, the reaction mixture was cooled to room temperature
  2. filtrationwas filtered off
  3. customThe filtrate was partitioned between ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=1:1)

来源与证据

ORD记录
ord-a6d16c84992d44c5ba2388e74f39994d
来源数据集
uspto-grants-2006_08
专利号
US07091352B2

关联笔记

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