Réaction #41702

Équation de réaction

tin(II) chloride dihydrate

sodium bicarbonate

4-methanesulfonyl-phenol

cesium carbonate

N-(4-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyrazine-2-carboxamide

→

6-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-(4-methanesulfonyl-phenoxy)-2-pyrazin-2-yl-1H-benzimidazole

Solvants

Ethyl acetate

N-methylpyrrolidinone

Conditions de réaction

Traitement

1. 1
   Autrethe reaction liquid
2. 2
   Autrethe reaction liquid
3. 3
   workup.STIRRINGwas stirred at 90° C. for 1 h our
4. 4
   workup.WAITat 100° C. for 2 hours
5. 5
   Autrethe resulting deposit was removed through filtration
6. 6
   Extractionextracted with ethyl acetate
7. 7
   Lavagethe organic layer was washed with water and saturated saline
8. 8
   Séchagedried with anhydrous magnesium sulfate
9. 9
   AutreThe solvent was evaporated away under reduced pressure
10. 10
    Autrepurified
11. 11
    Autrethrough partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1)
12. 12
    Autreto obtain the entitled compound as a pale yellow oily substance

Mode opératoire

9.2 mg of 4-methanesulfonyl-phenol and 26.2 mg of cesium carbonate were added to an N-methylpyrrolidinone (1 ml) solution of 10.4 mg of N-(4-((2R,5S)-1-acetyl-5-methylpyrrolidin-2-yl)-5-fluoro-2-nitrophenyl)pyrazine-2-carboxamide, and the reaction liquid was stirred at 90° C. for 1 hour. 60 mg of tin(II) chloride dihydrate was added to it, and the reaction liquid was stirred at 90° C. for 1 h our and at 100° C. for 2 hours. Ethyl acetate and aqueous saturated sodium bicarbonate were added to the reaction liquid, the resulting deposit was removed through filtration, extracted with ethyl acetate, and the organic layer was washed with water and saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and purified through partitioning thin-layer chromatography (Kieselgel™ 60F254, Art 5744 (by Merck), chloroform/methanol=10/1) to obtain the entitled compound as a pale yellow oily substance.

Source