反应详情

温度

25 °C

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionic acid (prepared as in Example 155A, 73 mg, 0.07 mmol) and triphenylphosphine (79 mg, 0.08 mmol) in methylene chloride (5.0 mL) was cooled to 0° C. and then treated with N-bromosuccinimide (60.5 mg, 0.34 mmol). The reaction mixture was stirred at 0° C. for 15 min and at 25° C. for 30 min. At this time, reaction mixture was treated with 2-amino-5-bromopyridine (52 mg, 0.30 mmol) and a few drops of pyridine. The resulting reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was then diluted with methylene chloride (50 mL). The organic phase was washed with water (1×35 mL) and a saturated aqueous sodium chloride solution (3×35 mL), dried over magnesium sulfate and sodium sulfate, treated with charcoal, filtered through a pad of celite, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70–230 mesh, 70/30 hexanes/ethyl acetate) afforded N-(5-bromo-pyridin-2-yl)-3-cyclopentyl-2-(4-methanesulfonyl-3-trifluoromethyl-phenyl)-propionamide (128.3 mg, quant) as a white solid: mp 81–85° C.; EI-HRMS m/e calcd for C21H22BrF3N2O3S (M+) 518.0486, found 518.0489.

1. customAt this time, reaction mixture
2. customThe resulting reaction mixture
3. stirringwas stirred at 25° C. for 18 h
4. washThe organic phase was washed with water (1×35 mL)
5. dry with materiala saturated aqueous sodium chloride solution (3×35 mL), dried over magnesium sulfate and sodium sulfate
6. additiontreated with charcoal
7. filtrationfiltered through a pad of celite
8. concentrationconcentrated in vacuo