反应详情

温度

90 °C

To a solution of (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one (112 mg, 0.259 mmol) in 1,4-dioxane (3 mL) was added 6-oxo-1,6-dihydropyridin-3-ylboronic acid (55 mg, 0.40 mmol), followed by Pd(dppf)Cl2 (11 mg, 0.015 mmol), and an aq solution of Cs2CO3 (0.48 mL, 2M in H2O). A reflux condenser was attached and the apparatus was degassed and flushed with N2 three times. The reaction was heated to 90° C. for 24 h. After cooling to rt the mixture was diluted with water and extracted three times with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by prep HPLC to afford the title compounds (21.6 mg) as an oil. LC-MS Method 1 tR=1.25 min, m/z=447, 389; 1H NMR (CD3OD) 0.96 (s, 3H), 1.28 (s, 3H), 1.57 (d, 3H), 2.16 (s, 2H), 2.21 (m, 1H), 2.46 (m, 2H), 3.03 (m, 1H), 5.57 (q, 1H), 6.66 (d, 1H), 7.02 (d, 2H), 7.25-7.40 (7H), 7.66 (s, 1H), 7.90 (d, 1H).

1. customA reflux condenser was attached
2. customthe apparatus was degassed
3. customflushed with N2 three times
4. temperatureAfter cooling to rt the mixture
5. additionwas diluted with water
6. extractionextracted three times with EtOAc
7. washThe organic layers were washed with brine
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated
11. customThe residue was purified by prep HPLC