反应详情

温度

70 °C

A sealed tube apparatus was charged with a solution containing 5-bromopyrimidine (1 g, 6.29 mmol), sodium carbonate (3.33 g, 31.4 mmol), and 3-cyano-2-fluorophenylboronic acid (1.037 g, 6.29 mmol) in a mixture of DME (Ratio: 2, Volume: 31.4 ml), water (Ratio: 1.000, Volume: 15.72 ml), and EtOH (Ratio: 1.000, Volume: 15.72 ml) at ambient temperature. Tetrakis(triphenylphosphine) palladium(0) (0.363 g, 0.314 mmol) was then added and the system was purged with nitrogen, sealed, and heated to 70° C. for 12 h. The vessel was cooled to room temperature and diluted with EtOAc and water. The mixture was further diluted with brine and extracted three times with EtOAc. The combined organics were dried over MgSO4, filtered, and concentrated to give the crude product. The crude material was purified by flash chromatography on silica using an ISCO machine (40 g SiO2 column, 40 mL/min, 0-40% EtOAc/hexanes over 15 minutes, tr=8 minutes) to afford the title compound (300 mg, 24%). ESI MS (M+H)+=200.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.28 (1 hr, s), 9.09 (2 hr, d, J=1.54 Hz), 8.02-8.12 (2 hr, m), 7.59 (1 hr, t, J=7.81 Hz).

1. additionA sealed tube apparatus was charged with a solution
2. customthe system was purged with nitrogen
3. customsealed
4. temperatureThe vessel was cooled to room temperature
5. additiondiluted with EtOAc and water
6. additionThe mixture was further diluted with brine
7. extractionextracted three times with EtOAc
8. dry with materialThe combined organics were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated
11. customto give the crude product
12. customThe crude material was purified by flash chromatography on silica using an ISCO machine (40 g SiO2 column, 40 mL/min, 0-40% EtOAc/hexanes over 15 minutes, tr=8 minutes)