反应详情

温度

80 °C

To a solution of 4-(1-methyl-1H-benzo[d]imidazol-2-ylamino)phenol (120 mg, 0.5 mmol) in DMSO (1 mL) was added cesium carbonate (196 mg, 0.6 mmol) and 2-fluoronicotinonitrile (61 mg, 0.5 mmol). The resulting mixture was heated to 80° C. for 16 h. After cooling to RT, the reaction mixture was diluted with EtOAc and washed with water and brine several times to remove DMSO. The aqueous layer was back extracted with EtOAc (3×) and the combined organic layer was dried (Na2SO4) and concentrated. The crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 0% to 5% of MeOH in CH2Cl2, followed by trituration with ether, to provide 2-(4-(1-methyl-1H-benzo[d]imidazol-2-ylamino)phenoxy)nicotinonitrile as off-white solid. MS (ESI, pos. ion) m/z: 342.2 (M+1). IC50 (uM) +++++.

1. temperatureAfter cooling to RT
2. washwashed with water and brine several times
3. customto remove DMSO
4. extractionThe aqueous layer was back extracted with EtOAc (3×)
5. dry with materialthe combined organic layer was dried (Na2SO4)
6. concentrationconcentrated
7. customThe crude product was chromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
8. washeluting with a gradient of 0% to 5% of MeOH in CH2Cl2