反应详情

温度

60 °C

To THF (16 mL) degassed by purging argon was added methyl 4-chloro-6-(4′-fluoro-[1,1′-biphenyl]-4-yl)picolinate (compound II, 800 mg, 0.83 mmol), vinyl boronic acid pinacol ester (360 mg, 2.9 mmol), and tetrabutylammonium fluoride (1M in THF, 4.68 mL), and the reaction mixture was degassed. Pd(dppf)Cl2 (85.6 mg, 0.04 mmol) was added and the reaction was degassed for an additional 15 minutes. The reaction mixture was heated at 60° C. in an oil bath for overnight. TLC (silica gel, 4/1 heptane/ethyl acetate) showed the reaction had not gone to completion. Additional reaction time had no effect, so the reaction was cooled, diluted with ethyl acetate, and extracted with brine. The organic layer was dried (sodium sulfate) and concentrated under vacuum to obtain the crude product which was purified by column chromatography (230-400 mesh silica gel, 0-8% ethyl acetate in heptane as eluent) to yield 600 mg of methyl 6-(4′-fluoro-[1,1′-biphenyl]-4-yl)-4-vinylpicolinate.

1. customTo THF (16 mL) degassed
2. customby purging argon
3. customthe reaction mixture was degassed
4. customthe reaction was degassed for an additional 15 minutes
5. temperatureso the reaction was cooled
6. additiondiluted with ethyl acetate
7. extractionextracted with brine
8. dry with materialThe organic layer was dried (sodium sulfate)
9. concentrationconcentrated under vacuum
10. customto obtain the crude product which
11. customwas purified by column chromatography (230-400 mesh silica gel, 0-8% ethyl acetate in heptane as eluent)