To a 5 mL glass microwave tube containing 5-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-indol-5-yl)-N-(2,2,2-trifluoroethyl)-1,3,4-oxadiazol-2-amine (180 mg, 0.320 mmol) was added 2-bromo-4-cyclopropylpyrimidine (73.3 mg, 0.368 mmol) (CombiPhos Catalysts Inc.), potassium phosphate (204 mg, 0.960 mmol) (Sigma-Aldrich), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (9.16 mg, 0.019 mmol) (Strem), and Pd2(dba)3 (8.79 mg, 9.60 μmol) (Strem). The tube was purged with argon, the solids were treated with dioxane (2.0 mL) and water (0.200 mL), the tube was sealed, and the contents were heated in an Initiator microwave reactor (Personal Chemistry, Biotage AB, Inc., Upssala, Sweden) at 100° 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 (20-100% EtOAc in Hex) affording 5-(3-(4-cyclopropylpyrimidin-2-yl)-1-tosyl-1H-indol-5-yl)-N-(2,2,2-trifluoroethyl)-1,3,4-oxadiazol-2-amine as an amorphous beige solid. MS (ESI, pos. ion) m/z: 554.9 (M+1). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.03 (s, 1H), 8.63-8.71 (m, 2H), 8.53 (s, 1H), 8.16 (d, J=8.8 Hz, 1H), 8.04 (m, J=8.4 Hz, 2H), 7.92 (d, J=7.2 Hz, 1H), 7.43 (m, J=8.2 Hz, 2H), 7.37 (d, J=5.1 Hz, 1H), 4.06-4.21 (m, 2H), 2.33 (s, 3H), 2.16-2.27 (m, 1H), 1.24 (br. s., 2H), 1.18 (d, J=6.7 Hz, 2H).
