Reaction Steps
To a microwave tube equipped with a stirring bar, (R)-4-((R)-1-((1-cyclopropyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one (120 mg, 0.292 mmol), 5-iodo-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (97.4 mg, 0. 0.35 mmol), 1,2-dimethoxyethane (2 mL), 1 N Na2CO3 aqueous solution (0.88 mL, 0.88 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (16.9 mg, 0.015 mmol) was added. The tube was sealed and heated in an oil bath at 100° C. for 2 hrs. DCM (200 mL) was added and the resulting mixture was washed with saturated NaHCO3 aqueous solution (20 mL×4), brine (20 mL×1), dried over anhydrous Na2SO4, filtered, removed solvents in vacuo. The resulting residue was passed a ISCO silica gel column (MeOH:DCM=5:95) to give white solids, 72.6 mg (yield 57.1%). 1H NMR (300 MHz, DMSO-d6) δ 8.18 (s, 1H), 7.59 (broad s, 1H), 7.53 (d, J=1.5 Hz, 1H), 7.21 (d, J=1.1 Hz, 1H), 6.82 (broad s, 1H), 6.31 (d, J=1.8 Hz, 1H), 4.78 (p, J=5.9 Hz, 1H), 4.51-4.34 (m, 1H), 3.98-3.84 (m, 2H), 3.73 (dddd, J=7.9, 3.9, 2.6, 0.6 Hz, 1H), 3.43-3.36 (m, 2H), 3.35 (m, 1H), 3.20-3.12 (m, 1H), 2.93-2.73 (m, 1H), 2.41-2.24 (m, 2H), 2.25-2.03 (m, 2H), 1.94-1.69 (m, 2H), 1.30 (d, J=5.9 Hz, 3H), 1.17-1.09 (m, 2H), 1.09-0.97 (m, 2H) ppm; MS (ESI+) m/z 436.16 (M+H).
