Reaktion #303158

Reaktionsgleichung

3-bromomethyl-5-chloro-benzo[b]thiophene

imidazo[1,2-a]pyridin-2-one hydrobromide salt

→

desired compound

3-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-one

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture is quenched with saturated ammonium chloride solution
2. 2
   ExtraktionThe product is extracted with ethyl acetate
3. 3
   WaschenThe organic layer is washed with water and brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe residue is purified by flash chromatography

Vorschrift

A mixture of 100 mg (0.47 mmol) of imidazo[1,2-a]pyridin-2-one hydrobromide salt and 122 mg (0.47 mmol) 3-bromomethyl-5-chloro-benzo[b]thiophene in 5 mL of THF is treated with 1 mL (1.0 mmol) of 1M lithium bis(trimethylsilyl)amide THF solution at −78° C. The resulting mixture is stirred this temperature for 1 h and the mixture is quenched with saturated ammonium chloride solution. The product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography to give the desired compound.

Quelle