Reaction #41695

Reaction equation

2-mercaptoethanol

potassium carbonate

N,N-dimethylformamide

6-(1-acetylpyrrolidin-2-yl)-5-(6-chloropyridin-3-yl)oxy-2-pyridin-2-yl-1H-benzimidazole

6-(1-Acetylpyrrolidin-2-yl)-5-((6-chloropyridin-3-yl)oxy)-2-pyridin-2-yl-1H-benzimidazole

→

compound

2-(5-((6-(1-Acetylpyrrolidin-2-yl)-2-pyridin-2-yl-1H-benzimidazol-5-yl)oxy)pyridin-2-ylsulfanyl)ethanol

Solvents

sodium bicarbonate

Conditions

Workup

1. 1
   Otherthe reaction liquid
2. 2
   TemperatureAfter cooled
3. 3
   Otherthe reaction liquid
4. 4
   Extractionextracted with chloroform
5. 5
   Dryingthe organic layer was dried with anhydrous magnesium sulfate
6. 6
   Otherthe solvent was evaporated away under reduced pressure
7. 7
   OtherThe resulting residue was purified
8. 8
   Otherthrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)

Procedure

20 mg of 2-mercaptoethanol and 10 mg of potassium carbonate were added in order to an N,N-dimethylformamide (1 ml) solution of 20 mg of 6-(1-acetylpyrrolidin-2-yl)-5-(6-chloropyridin-3-yl)oxy-2-pyridin-2-yl-1H-benzimidazole obtained in Example 504, and the reaction liquid was stirred at 120° C. for 5 hours. After cooled, the reaction liquid was diluted with aqueous saturated sodium bicarbonate, 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