Reacción #41635

Ecuación de reacción

tin(II) chloride dihydrate

4-fluoro-benzenethiol

potassium carbonate

pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide

→

compound

1-(2-(6-(4-fluoro-phenylsulfanyl)-2-pyridin-2-yl-3H-benzimidazol-5-yl)-pyrrolidin-1-yl)-ethanone

Disolventes

sodium bicarbonate

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe reaction liquid
2. 2
   Otrothe reaction liquid
3. 3
   workup.STIRRINGwas stirred at 100° C. for 3 hours
4. 4
   TemperaturaAfter cooled
5. 5
   Otrothe reaction liquid
6. 6
   Extracciónextracted with chloroform
7. 7
   Secadothe organic layer was dried with anhydrous magnesium sulfate
8. 8
   Otrothe solvent was evaporated away under reduced pressure
9. 9
   OtroThe resulting residue was purified
10. 10
    Otrothrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Procedimiento

20 mg of 4-fluoro-benzenethiol and 30 mg of potassium carbonate were added in order to an N,N-dimethylformamide (1 ml) solution of 50 mg of pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-5-fluoro-2-nitro-phenyl)-amide, and the reaction liquid was stirred at 100° C. for 2 hours. 30 mg of tin(II) chloride dihydrate was added to the reaction liquid, and the reaction liquid was stirred at 100° C. for 3 hours. After cooled, the reaction liquid was diluted with aqueous saturated sodium bicarbonate and extracted with chloroform, and the organic layer was dried with anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a white solid.

Fuente