N-tert-Butyl-5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (166 mg, 0.309 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (6.63 mg, 0.014 mmol) (Strem), Pd2(dba)3 (6.37 mg, 6.96 μmol) (Strem), potassium phosphate (148 mg, 0.696 mmol) (Sigma-Aldrich) and 2-chloro-5-fluoro-4-methoxypyrimidine (37.7 mg, 0.232 mmol) were weighed into a 5 mL glass microwave tube. The tube was purged with argon and the solids were treated with dioxane (2 mL) and water (0.200 mL). The tube was sealed, and the contents were heated an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 130° C. for 20 min. The mixture was treated with H2O and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The crude material was purified by flash chromatography (eluting with 5-60% EtOAc in Hex) to give N-tert-butyl-5-(3-(5-fluoro-4-methoxypyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-1,3,4-oxadiazol-2-amine (75.5 mg, 0.141 mmol, 60.7%) as an off white solid. MS (ESI, pos. ion) m/z: 537.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.98-9.03 (m, 1H), 8.72 (d, J=3.1 Hz, 1H), 8.56 (s, 1H), 8.16 (d, J=8.8 Hz, 1H), 8.02-8.07 (m, 2H), 7.86-7.92 (m, 1H), 7.64 (s, 1H), 7.40-7.48 (m, 2H), 4.22 (s, 3H), 2.33 (s, 3H), 1.35-1.41 (m, 9H).
