Nitrogen → HCID 117843836, compound

Participants

Reaction Conditions

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), 3-iodo-1-methyl-1H-pyrazole (121.4 mg, 0.584 mmol), 1,2-dimethoxyethane (3 mL), 1 N Na2CO3 aqueous solution (0.96 mL, 0.96 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (33.7 mg, 0.029 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, 40.5 mg (yield 38.0%). 1H NMR (300 MHz, DMSO-d6) δ 8.06 (s, 1H), 7.70 (d, J=2.2 Hz, 1H), 7.59 (broad s, 1H), 7.56 (d, J=1.1 Hz, 1H), 7.28 (broad s, 1H), 6.72 (d, J=2.2 Hz, 1H), 4.77 (m, 1H), 3.88 (s, 3H), 3.74-3.62 (m, 1H), 3.45-3.35 (m, 1H), 3.24-3.14 (m, 1H), 2.88-2.75 (m, 1H), 2.42-2.21 (m, 2H), 1.32 (d, J=6.0 Hz, 3H), 1.12-1.06 (m, 2H), 1.02 (m, 2H) ppm; MS (ESI+) m/z 366.34 (M+H).

Provenance & Evidence