Potassium Carbonate → HCID 21865136, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-[6-(quinolin-7-yloxy)-pyrimidin-4-yl]-5-trifluoromethyl-phenylamine, (Example 163), (0.25 g, 0.65 mmol), N,N-diisopropylethylamine (0.57 mL, 3.3 mmol) in 1,2-dichloroethane (6.5 mL) was added methanesulfonyl chloride (0.12 mL, 1.6 mmol, Aldrich). The mixture was stirred at 40° C. for 72 h. After cooling to room temperature, the reaction mixture was treated with satd NaHCO3 and H2O and extracted with EtOAc (2 ×75 mL). The combined extracts were washed with H2O (75 mL) and brine (75 mL), dried over Na2SO4, filtered, and concentrated onto silica gel. Purification by silica gel chromatography (gradient, 30 to 60% EtOAc/hexanes) afforded a pale yellow solid. To the solid was added MeOH (5 mL), CH2Cl2 (5 mL) and K2CO3 (0.050 g). The reaction mixture was stirred at room temperature for 24 h and then diluted with H2O and extracted with EtOAc (2×75 mL). The combined extracts were washed with H2O (75 mL), brine (75 mL), dried over Na2SO4, filtered, and concentrated onto silica gel. Purification by silica gel chromatography (gradient, 30 to 60% EtOAc/hexanes) afforded the title compound as a white solid. Mp: 203-204° C. MS (ESI, pos. ion) m/z: 461.0 (M+1).

Provenance & Evidence