Nitrogen → HCID 117843677, 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-1,5-dimethyl-1H-pyrazole (129.6 mg, 0.584 mmol), 1,2-dimethoxyethane (2 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 off-white solids, 69.2 mg (yield 62.5%). 1H NMR (300 MHz, DMSO-d6) δ 8.04 (s, 1H), 7.59 (broad s, 1H), 7.49 (d, J=1.1 Hz, 1H), 7.23 (d, J=1.2 Hz, 1H), 6.50 (s, 1H), 4.75 (p, J=6.0 Hz, 1H), 3.75 (s, 3H), 3.72-3.63 (m, 1H), 3.44-3.35 (m, 1H), 3.26-3.15 (m, 1H), 2.91-2.71 (m, 1H), 2.41-2.20 (m, 2H), 2.28 (s, 3H), 1.31 (d, J=6.0 Hz, 3H), 1.13-1.05 (m, 2H), 1.05-0.95 (m, 1H) ppm; MS (ESI+) m/z 381.01 (M+H).

Provenance & Evidence