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

HRID 1069643노트

반응식

HRID 1069643 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-40c8e0ce106f4ad480584aaba4f80c2c
출처 데이터셋
uspto-grants-2001_06
특허 번호
US06252084B1

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