Reaktion #429989

Reaktionsgleichung

1-(4-amino-benzyl)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester

triethylamine

2,2,2-trifluoroethanesulfonyl chloride

→

title compound

Ausbeute 105.4%

1-[4-(2.2.2-Trifluoro-ethanesulfonylamino)-benzyl]-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic Acid Ethyl Ester

Ausbeute 105.4%

Lösungsmittel

methylene chloride

methylene chloride

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at about -78° C. for about 45 minutes
2. 2
   WaschenThe organic layer was washed with brine
3. 3
   Trocknendried over sodium sulfate
4. 4
   Einengenconcentrated in vacuo to an oil
5. 5
   workup.STIRRINGtriethylamine (1 ml) and stirred for about two hours at room temperature
6. 6
   workup.ADDITIONThe mixture was poured into half-saturated ammonium chloride
7. 7
   Extraktionextracted into ethyl acetate
8. 8
   WaschenThe ethyl acetate was washed with brine
9. 9
   Trocknendried over sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Sonstigeevaporated

Vorschrift

To a solution of crude 1-(4-amino-benzyl)-5-(2-methyl-[1,3]dioxolan-2-ylmethyl)-1H-indole-2-carboxylic acid ethyl ester (2 g, ≈5 mmol) in methylene chloride (25 ml) stirring at about -78° C. under nitrogen was added triethylamine (1.28 g, 1.76 ml, 12.7 mmol). The mixture was stirred for about two minutes, and 2,2,2-trifluoroethanesulfonyl chloride (2.03 g, 1.23 ml, 12.7 mmol) was added dropwise via syringe over about five minutes. The mixture was stirred at about -78° C. for about 45 minutes, then diluted with methylene chloride and water and warmed to room temperature. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo to an oil. The oil was taken up in methanol (30 ml) and triethylamine (1 ml) and stirred for about two hours at room temperature. The mixture was poured into half-saturated ammonium chloride and extracted into ethyl acetate. The ethyl acetate was washed with brine, dried over sodium sulfate, filtered, and evaporated to give the title compound (2.85 g) as a foam containing some impurities, which was reacted without further purification.

Quelle