1-Bromo-3-methylbutane → HCID 11858031, compound

Participants

Reaction Conditions

Reaction Steps

In a 10 mL dry flask with stirring bar was placed {2-[4-(6,7-dimethoxy-quinolin-4-yloxy)-3-fluoro-phenyl]-pyrimidin-5-yl}-phenyl-amine (Example 39, 0.030 g, 0.06 mmol) under N2. Anhydrous THF (1.5 mL) was added, followed by the addition of NaH (60% dispersion, 0.10 g, 2.5 mmol). The resulting yellow mixture was heated at 50° C. for 20 min, then cooled to RT. 1-Bromo-3-methylbutane (0.20 mL) was added, and the resulting yellow mixture was heated at 50° C. for 4.5 h. The reaction was quenched with NH4Cl (half sat.) and the slurry was filtered, then washed with H2O. The brown solid was dissolved in CH2Cl2 and was purified on silica (50%-100% EtOAc in hexanes) to afford the title compound as a yellow solid. MS (ESI pos. ion) m/z: 539. Calc'd for C32H31FN4O3: 538.24.

Provenance & Evidence