Reaktion #485727

Reaktionsgleichung

2-amino-5-bromopyridine

N-bromosuccinimide

triphenylphosphine

2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid

→

2-(3-bromo-4-methanesulfonyl-phenyl)-N-(5-bromo-pyridin-2-yl)-3-cyclopentyl-propionamide

Ausbeute 58.4%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred at 0° C. for 5 min
3. 3
   Temperaturto warm to 25° C. where it
4. 4
   workup.STIRRINGwas stirred for 30 min
5. 5
   SonstigeThe resulting reaction mixture
6. 6
   workup.STIRRINGwas stirred at 25° C. for 15 h
7. 7
   SonstigeThe crude reaction mixture
8. 8
   Sonstigewas then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate)

Vorschrift

A solution of triphenylphosphine (154 mg, 0.59 mmol) in methylene chloride (3 mL) was cooled to 0° C. and then slowly treated with N-bromosuccinimide (104 mg, 0.59 mmol). The reaction mixture was stirred at 0° C. for 10 min and then treated with 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionic acid (prepared as in Example 72, 200 mg, 0.53 mmol). The resulting reaction mixture was stirred at 0° C. for 5 min and then allowed to warm to 25° C. where it was stirred for 30 min. The reaction mixture was then treated with 2-amino-5-bromopyridine (203 mg, 1.17 mmol). The resulting reaction mixture was stirred at 25° C. for 15 h. The crude reaction mixture was then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 3/1 hexanes/ethyl acetate) to afford the 2-(3-bromo-4-methanesulfonyl-phenyl)-N-(5-bromo-pyridin-2-yl)-3-cyclopentyl-propionamide (164 mg, 58%) as a white foam: mp 83-86° C. (foam to gel); FAB-HRMS m/e calcd for C20H22Br2N2O3S (M+H)+ 528.9796, found 528.9783.

Quelle