3-Fluoroaniline → HCID 11858025, compound

Participants

Reaction Conditions

Reaction Steps

The crude 2-chloro-5-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-3-methylpyrimidin-4(3H)-one from Step 3 was dissolved in 15 mL 1,4-dioxane. To 5 mL of this solution was added m-fluoroaniline (0.2 mL) and concentrated HCl (1 drop). The reaction was heated in the microwave at 60° C. and 60 W for 5 min before being cooled to RT. The mixture was concentrated and filtered through a 1 inch plug of silica gel with EtOAc→2:1 EtOAc/MeOH→3:2 MeOH/EtOAc. The filtrate was concentrated and purified using reverse phase HPLC (10%→95% MeCN/H2O with 0.1% TFA). Finally, the compound was filtered again through a 1-inch plug of silica gel in a pipette column with EtOAc to give the title compound. MS (ESI pos. ion) m/z: 517. Calc'd for C28H22F2N4O4: 516.16.

Provenance & Evidence