反应详情

An oven-dried flask was cooled under argon, then charged with anhydrous THF (40 mL) and 2-bromopyridine (1.76 mL, 18 mmol). Isopropylmagnesium chloride in tetrahydrofuran (2.0 M in THF, 11 mL) was then added dropwise at room temperature. The mixture was then stirred at room temperature for 2 hours, then cooled to 0° C., whereupon a THF solution (5 mL) of 5-bromo-2-fluoro-N-methoxy-N-methylbenzamide (3.93 g, 15 mmol) was added. The mixture was then allowed to warm to room temperature and stirred for 2 hours. The reaction was quenched with saturated NH4Cl, extracted with EtOAc, washed with 10% HCl, dried over Na2SO4, and purified by column chromatography (gradient 0 to 10% EtOAc/hexanes) to afford the product. 1H NMR (400 MHz, CDCl3) δ 8.69 (d, J=4.6 Hz, 1H), 8.09 (d, J=7.8 Hz, 1H), 7.92 (t, J=7.7 Hz, 1H), 7.79 (dd, J=5.8, 1.4 Hz, 1H), 7.67-7.59 (m, 1H), 7.52 (dd, J=7.4, 4.9 Hz, 1H), 7.04 (t, J=9.0 Hz, 1H).

1. temperatureAn oven-dried flask was cooled under argon
2. additionwas added
3. temperatureto warm to room temperature
4. stirringstirred for 2 hours
5. customThe reaction was quenched with saturated NH4Cl
6. extractionextracted with EtOAc
7. washwashed with 10% HCl
8. dry with materialdried over Na2SO4
9. custompurified by column chromatography (gradient 0 to 10% EtOAc/hexanes)
10. customto afford the product