反应详情

温度

80 °C

To a solution of (4S,5R)-5-[3,5-bis(trifluoromethyl)phenyl]-3-(2-bromo-5-nitrobenzyl)-4-methyl-1,3-oxazolidin-2-one (950 mg, 1.80 mmol) in a toluene (5.2 mL): ethanol (2.6 mL): water (1.3 mL) mixture was added (2-chloro-5-isopropylphenyl)boronic acid (325 mg, 1.64 mmol), tetrakis(triphenylphosphine)palladium(0) (188 mg, 10 mol %) and sodium carbonate (346 mg, 3.26 mmol). The resulting mixture was heated in an 80° C. oil bath for 12 h. The reaction crude was evaporated into dryness. The resulting residue was taken up by a mixture of water and EtOAc. The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to give the crude product, which was purified by SiO2 (Biotage 40+S cartridge, EtOAc/hexane, gradient) to afford the titled compound. LC-MS: 601.19 (M+1)+. 1H NMR (CDCl3, 500 MHz) a 1:1 mixture of rotamers δ 8.31-8.30 (m, 1 H), 8.24-8.28 (m, 1 H), 7.85-7.89 (m, 1 H), 7.68-7.76 (m, 2 H), 7.42-7.48 (m, 2 H), 7.26-7.30 (m, 1 H), 7.04-7.11 (m, 1 H), 5.74 (d, J=7.8 Hz, 0.5 H), 5.58 (d, J=8.0 Hz, 0.5 H), 4.92 (d, J=15.8 Hz, 0.5H), 4.76 (d, J=16.2 Hz, 0.5H), 3.97-4.04 (m, 1.5 H), 3.82 (dt, J=8.0, 6.6 Hz, 0.5H), 2.89-2.99 (m, 1H) 1.22-1.29 (m, 6 H), 0.60 (d, J=6.4 Hz, 1.5 H), 0.52 (d, J=6.6 Hz, 1.5 H).

1. customThe reaction crude
2. customwas evaporated into dryness
3. additionThe resulting residue was taken up by a mixture of water and EtOAc
4. dry with materialThe combined organic extracts were dried over Na2SO4
5. concentrationconcentrated in vacuo
6. customto give the crude product, which
7. customwas purified by SiO2 (Biotage 40+S cartridge, EtOAc/hexane, gradient)