Potassium Carbonate → HCID 68551673, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 6-(5-bromo-pyridin-2-yloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (200 mg, 0.515 mmol), N-{3-[3,5-difluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (238 mg, 0.60 mmol) (Biswajit et. al. WO 2006038100 A1 and Gravestock et. al. WO2004/078753 A1), Pd(Ph3P)4(70 mg) and K2CO3 (150 mg) in DMF/H2O (10/1.5.5 mL) was degassed. The mixture was heated to 80° C. for 2 h, diluted with EtOAc, washed with brine and concentrated in vacuo to give a crude product. The crude product was purified by flash chromatography (5% MeOH in EtOAc) to afford the title product (117 mg, 43%). ESI MS m/z 531.5 (M+H+). 1H NMR (400 MHz, DMSO) δ 8.30 (s, 1H), 8.28 (t, J=6.0 Hz, 1H), 8.07 (s, 1H), 7.93 (s, 1H), 7.85 (d, J=8.8 Hz, 1H), 7.46 (d, J=10.4 Hz, 1H), 7.00 (d, J=8.8 Hz, 1H), 5.77 (s, 1H), 4.80-4.68 (m, 3H), 4.48-4.40 (m, 2H), 4.14 (t, J=9.4 Hz, 1H), 3.75 (dd, J=9.2, 6.4 Hz, 1H), 3.41 (t, J=5.4 Hz, 2H), 1.82 (s, 3H).

Provenance & Evidence