乙酸乙酯 → 3-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

HRID 1007484笔记

反应方程式

HRID 1007484 反应方程式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[CH:22]=[C:23]([N+:29]([O-:31])=[O:30])[CH:24]=[C:25]([CH3:28])[C:26]=1F.C(OCC)(=O)C>CS(C)=O.O>[CH:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:26]3[C:21]([CH3:20])=[CH:22][C:23]([N+:29]([O-:31])=[O:30])=[CH:24][C:25]=3[CH3:28])[CH:3]=2)[NH:7][CH:6]=1)([CH3:13])[CH3:12]

参与物

7

反应物 4

HCID 8857乙酸乙酯HCID 11430碳酸钾HCID 113672322-氟-1,3二甲基-5-硝基苯HCID 226694913-isopropyl-1H-indol-5-ol

产物 1

HCID 226695113-Isopropyl-5-(4-nitro-2,6-dimethyl-phenoxy)-1H-indole

试剂、催化剂与溶剂 2

HCID 679二甲基亚砜溶剂HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂

反应条件

温度
100 °C

实验过程

11.44 g (58.76 mmol) of 5-hydroxy-3-isopropyl-indole are dissolved in 350 ml of DMSO, 8.93 g (64.63 mmol) of potassium carbonate in solid form are introduced and subsequently 9.94 g (58.76 mmol) of 3,5-dimethyl-4-fluoronitrobenzene are added. The reaction solution is stirred for 2 hours at 100° C. under argon. Afterwards it is cooled to room temperature, 100 ml of ethyl acetate and 600 ml of H2O are added; ethyl acetate is separated off after phase separation and the aqueous phase is reextracted twice with ethyl acetate. The combined organic phases are washed twice with sodium chloride solution, dried over sodium sulphate, filtered and concentrated to dryness. The residue is purified by chromatography on silica gel by means of cyclohexane/ethyl acetate (10:1).

后处理

  1. temperatureAfterwards it is cooled to room temperature
  2. customethyl acetate is separated off
  3. customafter phase separation
  4. washThe combined organic phases are washed twice with sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue is purified by chromatography on silica gel by means of cyclohexane/ethyl acetate (10:1)

来源与证据

ORD记录
ord-c65647b50728423e988ab1d275144b03
来源数据集
uspto-grants-2004_09
专利号
US06794406B2

反应笔记

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