二氧化硒 → 3-溴-2-甲酰基吡啶

HRID 7152

反应方程式

HRID 7152 反应方程式
[Br:1][C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[Se](=O)=[O:10]>O1CCOCC1>[Br:1][C:2]1[C:3]([CH:8]=[O:10])=[N:4][CH:5]=[CH:6][CH:7]=1

参与物

4

反应物 2

HCID 24007二氧化硒HCID 12010032-甲基-3-溴吡啶

产物 1

HCID 164142313-溴-2-甲酰基吡啶收率 29%

试剂、催化剂与溶剂 1

HCID 312751,4-二氧六环溶剂

实验过程

To a solution of 3-bromo-2-picoline (prepared as described by Guthikonda, R. N.; Cama, L. D.; Quesada, M.; Woods, M. F.; Salzmann, T. N.; Christensen, B. G. J. Med. Chem. 1987, 30, 871–880) (249 mg, 1.45 mmol) in dioxane (2 mL) was added selenium(IV) oxide (212 mg, 1.91 mmol) and the mixture stirred at reflux overnight. The reaction mixture was concentrated under reduced pressure and purified by column chromatography on silica gel (Hexanes/ether, 3:1) to afford the title compound (78 mg, 29%) as a pale yellow solid. 1H NMR (CDCl3): δ 7.38 (dd, 1H, J=9, 6 Hz), 8.05 (d, 1H, J=9 Hz), 8.76 (d, 1H, J=3 Hz), 10.25 (s, 1H).

后处理

  1. temperatureat reflux overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by column chromatography on silica gel (Hexanes/ether, 3:1)

来源与证据

ORD记录
ord-493790f571d847c0aaa1ed77fe3bc67c
来源数据集
uspto-grants-2006_08
专利号
US07084155B2

关联笔记

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