反应详情

温度

0 °C

To a solution of N-(2-bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl -3-trifluoromethyl-benzenesulfonamide (984 mg, 2.0 mmol) in THF (10 mL) under nitrogen atmosphere at 0° C. was added dropwise isopropylmagnesium chloride (2 M solution in THF, 2.5 mL, 5.0 mmol). The mixture was then stirred for 30 min at 0° C. followed by the addition of 2-chloro-N-methoxy -3,N-dimethyl-benzamide (852 mg, 4.0 mmol) at 0° C. The mixture was stirred at room temperature for 3 h, quenched with saturated aqueous NH4Cl solution (5 mL), and extracted with EtOAc (2×25 mL). The combined organic layers were washed with saturated aqueous NH4Cl solution (25 mL), brine (25 mL), dried (anhydrous Na2SO4) and concentrated under reduced pressure. The residue was column purified (SiO2, 50% EtOAc-hexanes) to obtain 4-chloro-N-[5-chloro-2-(2-chloro-3-methyl-benzoyl)-pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (586 mg) in 52% yield. ESMS m/z (relative intensity): 534.9 [(M-32+H)]+ (70), 588.9 (M+Na)+.

1. stirringThe mixture was stirred at room temperature for 3 h
2. customquenched with saturated aqueous NH4Cl solution (5 mL)
3. extractionextracted with EtOAc (2×25 mL)
4. washThe combined organic layers were washed with saturated aqueous NH4Cl solution (25 mL), brine (25 mL)
5. dry with materialdried (anhydrous Na2SO4)
6. concentrationconcentrated under reduced pressure
7. custompurified (SiO2, 50% EtOAc-hexanes)