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

HRID 1069643ノート

反応式

HRID 1069643 の反応式
[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

参加物

6

反応物 3

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 107537632-cyclopropyl-5-methoxyl-1H-indole-3-acetic acid methyl ester

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-40c8e0ce106f4ad480584aaba4f80c2c
出典データセット
uspto-grants-2001_06
特許番号
US06252084B1

反応ノート

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