反应详情

温度

0 °C

A solution of isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 8.5 mL, 11.0 mmol) was added to a solution of 4-iodo-2-(trifluoromethyl)pyridine (3.0 g, 11.0 mmol) in tetrahydrofuran (10 mL) cooled to 0° C. After 10 minutes, the solution was stirred at 23° C. for 35 min. The dark reddish brown solution was then cooled to −78° C. A solution of 5-ethoxy-2-(4-fluorophenyl)-N-methoxy-N-methyl-2H-1,2,3-triazole-4-carboxamide (i.e. the product of Step B, 2.5 g, 8.5 mmol) in tetrahydrofuran (25 mL) was added. The solution was stirred at 23° C. for 22 h. The reaction was quenched by the addition of a saturated aqueous ammonium chloride solution (10 mL) and water (10 mL). The mixture was extracted with ethyl acetate (2×40 mL), dried (MgSO4) and concentrated under reduced pressure to obtain the crude product. The crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes to afford the title compound (1.8 g) as a colorless solid.

1. temperatureThe dark reddish brown solution was then cooled to −78° C
2. stirringThe solution was stirred at 23° C. for 22 h
3. customThe reaction was quenched by the addition of a saturated aqueous ammonium chloride solution (10 mL) and water (10 mL)
4. extractionThe mixture was extracted with ethyl acetate (2×40 mL)
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure
7. customto obtain the crude product
8. customThe crude residue was purified by chromatography on silica gel eluting with 0 to 20% ethyl acetate in hexanes