Réaction #41635

Équation de réaction

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

Solvants

sodium bicarbonate

N,N-dimethylformamide

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source