To a vial charged with (S)-3-(4-bromophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.100 mg, 0.289 μmol), potassium carbonate (0.120 mg, 0.867 mol), copper (I) iodide (0.055 mg, 0.289 μmol), and 1H-imidazo[4,5-c]pyridin-2(3H)-one (commercially available from Prime Organics Inc. Woburn, Mass.) (117 mg, 0.867 μmol) were added n-butanol (1.155 μL) and N1,N2-dimethylethane-1,2-diamine (0.051 mg, 0.578 μmol). The suspension was purged with nitrogen, and then sealed and shaken overnight at 110° C. The resulting suspension was cooled to room temperature and filtered through Celite® brand filter aid. The filtrate was dried under reduced pressure and the residue was dissolved in DMSO and purified using RP-HPLC ramping ACN in H2O (10-90%, 0.1% TFA throughout). Separation of isomers was accomplished and the respective product containing eluents were dried under reduced pressure providing products which were lyophilized from MeOH/H2O providing (S)-5,5-dimethyl-3-(4-(2-oxo-1H-imidazo[4,5-c]pyridin-3(2H)-yl)phenyl)-4-phenyloxazolidin-2-one (5 mg, 4%) as a yellow solid and (S)-5,5-dimethyl-3-(4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)phenyl)-4-phenyloxazolidin-2-one (5 mg, 4%) as a light brown solid. Structures were assigned arbitrarily. Data for product A: 1H NMR (500 MHz, DMSO-d6) δ=8.22 (d, J=5.2 Hz, 1H), 8.14 (s, 1H), 7.69-7.64 (m, 2H), 7.51 (d, J=9.0 Hz, 2H), 7.42-7.38 (m, 2H), 7.35-7.28 (m, 3H), 7.12 (d, J=5.2 Hz, 1H), 5.51 (s, 1H), 1.66 (s, 3H), 0.93 (s, 3H). m/z (ESI) 401.2 (M+H)+. Data for product B: 1H NMR (500 MHz, DMSO-d6) δ=8.29 (s, 1H), 8.18 (s, 1H), 7.67 (d, J=9.0 Hz, 2H), 7.47 (d, J=8.9 Hz, 2H), 7.42-7.38 (m, 2H), 7.35-7.28 (m, 3H), 6.99 (d, J=5.4 Hz, 1H), 5.51 (s, 1H), 1.66 (s, 3H), 0.93 (s, 3H). m/z (ESI) 401.2 (M+H)+.
