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

HRID 1069643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1069643
[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

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-40c8e0ce106f4ad480584aaba4f80c2c
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06252084B1

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