Reaktion #87029

Reaktionsgleichung

ethyl 5-(3,4-dichlorobenzyl)-1,2,4-oxadiazole-3-carboxylate

HATU

N,N diisopropylethylamine

2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride

→

N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(3,4-dichlorobenzyl)-1,2,4-oxadiazole-3-carboxamide

Ausbeute 32.4%

Lösungsmittel

methanol

sodium hydroxide

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was prepared
2. 2
   SonstigeThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Vorschrift

This compound was prepared according to method F with ethyl 5-(3,4-dichlorobenzyl)-1,2,4-oxadiazole-3-carboxylate (0.130 g; 0.433 mmol) in methanol (2 mL) and sodium hydroxide in water (2M, 2 mL); and 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.433 mmol), HATU (0.164 g; 0.432 mmol), N,N diisopropylethylamine (0.075 mL; 0.432 mmol) in DMF (4 mL). The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.063 g (32%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(3,4-dichlorobenzyl)-1,2,4-oxadiazole-3-carboxamide as a white solid.

Quelle