氢化钠 → 1-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester

HRID 1069606笔记

反应方程式

HRID 1069606 反应方程式
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[NH:8][C:7]=1[CH3:17])[CH3:2].[H-].[Na+].Br[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:7]=1[CH3:17])[CH3:2]

参与物

5

反应物 3

HCID 24758氢化钠HCID 2633652-苯基溴化甲基苯HCID 10729163(5-甲氧基-2-甲基-1H-吲哚-3-基)-乙酸乙酯

产物 1

HCID 107642291-([1,1'-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester收率 72%

试剂、催化剂与溶剂 1

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

实验过程

1-([1,11′-Biphenyl]-2-ylmethyl)-5-methoxy,y-2-methyl-1H-indole-3-acetic acid ethyl ester. 5-Methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester (988 mg, 4 mmol) was added to 160 mg (4 mmol) of NaH/mineral oil (previously washed with hexane), the mixture stirred for 0.5 hours and 0.74 mL (4 mmol) of2- (bromomethyl) biphenyl added. After 2 hours, water was added and the mixture extracted with ethyl acetate. The ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel eluting with 20% EtOAc/hexane to give 1.18 g (72% yield) of 1-([1,1′-biphenyl]-2-ylmethyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester as an oil.

后处理

  1. washpreviously washed with hexane), the mixture
  2. waitAfter 2 hours
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe ethyl acetate was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated at reduced pressure
  7. customThe residue was chromatographed on silica gel eluting with 20% EtOAc/hexane

来源与证据

ORD记录
ord-7116ac58940b4af186b494fa8da01608
来源数据集
uspto-grants-2001_06
专利号
US06252084B1

反应笔记

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