5-[4-(1,1-Dioxidothiomorpholin-4-yl)phenyl]-2-nitrothiophene-3-carboxamide (Intermediate 16) (525 mg, 1.376 mmol) and Pt/C, doped with V (90 mg, 0.014 mmol) were stirred at room temperature overnight in degassed MeOH (5 mL) under a balloon of H2. The vial was then evacuated and back-filled with N2 (4×) and 1-[(6-bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol (Example 217 Step 1) (358 mg, 1.38 mmol), Pd2dba3 (126 mg, 0.138 mmol), X-Phos (328 mg, 0.69 mmol) and K2CO3 (209 mg, 1.51 mmol) were added. The vial was evacuated and back-filled with N2 (3×) and the resulting mixture was stirred at 100° C. for 4 hours. After cooling to room temperature, the mixture was diluted with methanol, silica gel was added, and the solvent was removed in vacuo. Purification of the residue by silica gel chromatography (0-6% MeOH—CHCl3) gave the title compound as a beige solid after triturating in DCM.
