Reaction Steps
A mixture of (S)—N-((3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-2-oxooxazolidin-5-yl)methyl)acetamide (0.14 g, 0.37 mmol) and 2-((5-bromopyrimidin-2-yloxy)methyl)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole (0.105 g, 0.29 mmol) in toluene (2.5 mL), EtOH (1.5 mL), DMF (4 mL) and K2CO3 (2 M, 1 mL, 2 mmol) was purged with nitrogen. PdCl2(dppf) (12 mg, 0.015 mmol) was added and the mixture was refluxed (100° C.) under nitrogen for 1 h, then partitioned between EtOAc (150 mL) and water (100 mL). The aqueous layer was re-extracted with 100 mL EtOAc. The organic layer was washed with brine, dried (Na2SO4) and evaporated, column chromatography using gradient elution (DCM/MeOH 0 to 5%) gave the title compound as a brown solid (60 mg, 39%). APCI MS m/z 528.3 (M+H). 1H NMR (400 MHz, (CD3)2SO) δ 8.81 (d, J=1.3 Hz, 2H), 8.22 (t, J=5.8 Hz, 1H), 8.16 (s, 1H), 7.68 (t, J=8.8 Hz, 1H), 7.65 (dd, J=13.4, 2.2 Hz, 1H), 7.45 (dd, J=8.6, 2.2 Hz, 1H), 4.81-4.73 (m, 1H), 4.71 (d, J=11.9 Hz, 1H), 4.67 (d, J=11.9 Hz, 1H), 4.45 (d, J=11.0 Hz, 1H), 4.23 (d, J=11.0 Hz, 1H), 4.18 (t, J=9.1 Hz, 1H), 3.79 (dd, J=9.2, 6.4 Hz, 1H), 3.44 (t, J=5.5 Hz, 2H), 1.84 (s, 3H), 1.73 (s, 3H).
