反应详情

(E)-N-((2-cyanophenyl)(2,6-dichloropyridin-4-yl)methylene)-2-methylpropane-2-sulfinamide (Scheme #19, B, 0.69 g, 1.81 mmol) was dissolved in dry tetrahydrofuran (20 mL) at 0° C. to which a solution of 3-methoxyphenylmagnesium bromide (1.0 M in tetrahydrofuran, 5.44 mL, 5.44 mmol) in tetrahydrofuran was added. The reaction was stirred for 50 minutes and then quenched by addition of saturated aqueous ammonium chloride (25 mL), then further diluted with saturated aqueous sodiumhydrogen carbonate and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and evaporated. The residue was dissolved in methanol (20 mL) and treated with hydrochloride (1.0 M in diethyl ether, 3.63 mL, 3.63 mmol) for 1.5 h and then treated with saturated aqueous sodiumhydrogen carbonate and washed with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and evaporated. Purification by flash chromatography using ethyl acetate afforded 0.621 g (89% yield) of the title compound. 1H NMR (CDCl3) δ 7.59-7.43 (m, 4 H), 7.29-7.20 (m, 3 H), 6.89-6.87 (m, 3 H), 3.75 (s, 3 H). MS (AP) m/z 384 [M+1]+.

1. additionwas added
2. customquenched by addition of saturated aqueous ammonium chloride (25 mL)
3. additionfurther diluted with saturated aqueous sodiumhydrogen carbonate
4. extractionextracted with ethyl acetate
5. dry with materialThe organic phase was dried over magnesium sulfate
6. customevaporated
7. dissolutionThe residue was dissolved in methanol (20 mL)
8. washwashed with ethyl acetate
9. washThe organic phase was washed with brine
10. dry with materialdried over sodium sulfate
11. customevaporated
12. customPurification by flash chromatography