氯化苄 → 2-cyclopropyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester

HRID 1069643笔记

反应方程式

HRID 1069643 反应方程式
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[NH:7][C:6]=1[CH:16]1[CH2:18][CH2:17]1.[H-].[Na+].[CH2:22](Cl)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[N:7]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:6]=1[CH:16]1[CH2:17][CH2:18]1

参与物

6

反应物 3

HCID 7503氯化苄HCID 24758氢化钠HCID 107537632-cyclopropyl-5-methoxyl-1H-indole-3-acetic acid methyl ester

产物 1

HCID 108316472-cyclopropyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester收率 40%

试剂、催化剂与溶剂 2

HCID 962聚[6-[4-(4-氰基苯基)苯氧基]己基甲基丙烯酸酯]溶剂HCID 6228N,N-二甲基甲酰胺溶剂

实验过程

A solution of 3.8 g (146 mmol) of 2-cyclopropyl-5-methoxyl-1H-indole-3-acetic acid methyl ester in 50 mL of DMF was treated with 0.59 g (0146 mol) of 60% NaH/mineral oil, stirred 0.5 hour, and 1.69 mL (146 mmol) of benzyl chloride added. After 20 hours, the reaction mixture was diluted with water, extracted with EtOAc, the EtOAc solution was washed four times with water and dried over Na2SO4. After concentrating at reduced pressure, the product was purified by chromatography on silica, eluting with a gradient, 5% EtOAc/toluene→15% EtOAc/toluene, to give 2.05 g (40% yield) of 2-cyclopropyl-5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid methyl ester as an oil.

后处理

  1. waitAfter 20 hours
  2. extractionextracted with EtOAc
  3. washthe EtOAc solution was washed four times with water
  4. dry with materialdried over Na2SO4
  5. concentrationAfter concentrating at reduced pressure
  6. customthe product was purified by chromatography on silica
  7. washeluting with a gradient, 5% EtOAc/toluene→15% EtOAc/toluene

来源与证据

ORD记录
ord-40c8e0ce106f4ad480584aaba4f80c2c
来源数据集
uspto-grants-2001_06
专利号
US06252084B1

反应笔记

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