反应详情

A mixture of 6-allyl-3-[1-(4-bromo-phenyl)-ethyl]-6-isopropyl-[1,3]oxazinan-2-one (200 mg, 0.55 mmol), 2,4-difluorophenylboronic acid (104 mg, 0.66 mmol), PdCl2(PPh3)2 (20 mg), aqueous Cs2CO3 solution (2 M, 2 mL) in 1,4-dioxane (8 mL) was heated to reflux for 2 h. The mixture was filtered, and the filtrate was extracted with EtOAc for 3 times. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated to give the crude product, which was purified by preparative TLC to give 6-allyl-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-isopropyl-1,3-oxazinan-2-one (160 mg, 73%). 1H NMR (CDCl3): 0.96 (m, 6H), 1.61 (m, 3H), 1.68-2.09 (m, 3H), 2.32-2.47 (m, 2H), 2.84 (m, 1H), 3.18 (m, 1H), 5.02-5.19 (m, 2H), 5.84 (m, 2H), 6.93 (m, 2H), 7.41 (m, 3H), 7.50 (m, 2H).

1. temperaturewas heated
2. temperatureto reflux for 2 h
3. filtrationThe mixture was filtered
4. extractionthe filtrate was extracted with EtOAc for 3 times
5. washThe combined organic layer was washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customto give the crude product, which
9. customwas purified by preparative TLC