To a round bottom flask equipped with a magnetic stir bar was added 3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-phenylamine (0.141 mg, 0.57 mmol, 1.0 eq.), 1-(4-fluoro-phenylcarbamoyl)-carboxylic acid (0.193 g, 0.88 mmol), HATU (0.584 g, 1.14 mmol), triethylamine (0.23 ml, 1.3 mmol) and anhydrous DMF (5 ml). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with H2O (100 ml) and extracted with CHCl3 (3×). The combined organic extractions were washed with H2O (1×), sat'd NaHCO3 (2×), 10% LiCl (3×), sat'd NaCl (1×), dried (Na2SO4), and concentrated in vacuo. The resulting crude residue was purified by HPLC to yield N-(4-fluorophenyl)-N′-[3-fluoro-4-(7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)phenyl]propanediamide as a white solid (0.051 g, 21% yield). 1H NMR (400 MHz, DMSO): 12.30 (s, 1H), 10.49 (s, 1H), 10.28 (s, 1H), 8.29(s, 1H), 7.80 (dd, 1H), 7.65 (m, 2H), 7.51 (m, 1H), 7.40 (m, 2H), 7.19 (m, 2H), 6.58 (d, 1H), 3.49 (s, 2H); MS (ESI) for C21H15F2N5O3: 424 (MH+).
