反应详情

A mixture of (6S)-6-[(5-bromo-2-thienyl)methoxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.200 g, 0.555 mmol) and N-({(5S)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide (0.252 g, 0.666 mmol) in EtOH (3 mL), toluene (5 mL), DMF (8 mL) and K2CO3 (2 mL, 2 M, 4 mmol) was purged with nitrogen. PdCl2(dppf) (23 mg, 0.03 mmol) was added and the mixture was refluxed under nitrogen for 1 h then partitioned between EtOAc and water. Column chromatography (9:1 DCM/MeOH) gave a solid which was then reprecipitated from DCM/MeOH to give the titled compound (0.142 g, 48%) as a pale grey solid. APCI MS m/z 532 (M+H). 1H NMR (400 MHz, DMSO-d6) δ 8.21 (t, J=5.7 Hz, 1H), 8.02 (s, 1H), 7.76 (t, J=8.9 Hz, 1H), 7.59 (dd, J=14.0, 2.1 Hz, 1H), 7.36-7.43 (m, 2H), 7.13 (d, J=3.3, 1H), 4.87 (d, J=13.6 Hz, 1H), 4.84 (d, J=13.6 Hz, 1H), 4.72-4.80 (m, 1H), 4.64 (bd, J=12.4 Hz, 1H), 4.47 (d, J=11.9 Hz, 1H), 4.21-4.30 (m, 3H), 4.15 (t, J=9.1 Hz, 1H), 3.74-3.81 (m, 1H), 3.43 (t, J=5.4 Hz, 2H), 1.84 (s, 3H).

1. customwas purged with nitrogen
2. temperaturethe mixture was refluxed under nitrogen for 1 h
3. customthen partitioned between EtOAc and water
4. customColumn chromatography (9:1 DCM/MeOH) gave a solid which
5. customwas then reprecipitated from DCM/MeOH