反应详情

温度

100 °C

To a degassed solution of 6-((6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline (10 mg, 0.03 mmol) in DMF (1 mL) was added Pd(Ph3P)4 (3.1 mg, 2.65 μmol). After stirring for 20 min, tributyl(1-ethoxyvinyl)stannane (14.4 mg, 0.04 mmol) was added. The reaction was heated at 100° C. until the LC-MS showed its completetion. The reaction mixture was filtered through celite and washed with ether. The filtration was washed with water, dried over Na2SO4, and concentrated. The crude product was purified by column chromatography with hexane:EtOAc to give 6-((6-(1-ethoxyvinyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)-5,7-difluoroquinoline (6.0 mg, 61%). 1H-NMR (400 MHz, CDCl3) δ ppm 9.16 (s, 1H), 8.98 (d, 1H), 8.43 (d, 1H), 7.65 (d, 1H), 7.48 (m, 1H), 6.17 (s, 2H), 5.60 (s, 1H), 4.57 (s, 1H), 4.04 (q, 2H), 1.49 (t, 3H). LCMS (method B): [MH]+=369.0, tR=2.45 min.

1. filtrationThe reaction mixture was filtered through celite
2. washwashed with ether
3. filtrationThe filtration
4. washwas washed with water
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customThe crude product was purified by column chromatography with hexane