1-硝基丙烷 → 7-bromo-5-chloro-1H-indole-3-carbonitrile

HRID 913965

反应方程式

HRID 913965 反应方程式
[Br:1][C:2]1[CH:3]=[C:4]([Cl:13])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH:11]=O.P([O-])([O-])([O-])=O.[NH4+].[NH4+].[NH4+].[N+:22](CCC)([O-])=O>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([Cl:13])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[C:11]#[N:22]

参与物

5

反应物 3

HCID 79031-硝基丙烷HCID 159282磷酸铵HCID 575461137-bromo-5-chloro-1H-indole-3-carbaldehyde

产物 1

HCID 575462207-bromo-5-chloro-1H-indole-3-carbonitrile收率 54.5%

试剂、催化剂与溶剂 1

HCID 176醋酸溶剂

实验过程

A mixture of 7-bromo-5-chloro-1H-indole-3-carbaldehyde (0.80 g, 3.09 mmol), Ammonium phosphate, dibasic (1.269 mL, 15.47 mmol), and 1-nitropropane (0.276 mL, 3.09 mmol) in Acetic Acid (20 mL) was heated at reflux. The solvent was evaporated, the residue was taken up in aqueous sodium bicarbonate (300 mL) and extracted with ethyl acetate (3×20 mL). The organic layers were dried with MgSO4 and evaporated. The residue was purified by chromatography on SiO2 with 20%-25% ethyl acetate/hexanes to give 7-bromo-5-chloro-1H-indole-3-carbonitrile (0.43 g, 1.683 mmol, 54.4% yield) as a yellow solid. 1H-NMR (CDCl3, 400 MHz) δ 8.27 (bs, 1H), 7.79 (s, 1H), 7.72 (d, J=1.8 Hz, 1H), 7.49 (d, J=1.8 Hz, 1H). LC/MS (HPLC method 4): tR=3.12 min, 255.01(MH)+.

后处理

  1. temperaturewas heated
  2. temperatureat reflux
  3. customThe solvent was evaporated
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe organic layers were dried with MgSO4
  6. customevaporated
  7. customThe residue was purified by chromatography on SiO2 with 20%-25% ethyl acetate/hexanes

来源与证据

ORD记录
ord-b014e68c04824017b8e7a4fd2023d96d
来源数据集
uspto-grants-2011_09
专利号
US08026257B2

关联笔记

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