Nitrogen → HCID 117842677, 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), 2-bromo-5-methyl-1,3,4-thiadiazole (104.5 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 light yellow solids, 58.1 mg (yield 51.9%). 1H NMR (300 MHz, DMSO-d6) δ 8.22 (s, 1H), 7.69 (d, J=1.2 Hz, 1H), 7.60 (broad s, 1H), 7.44 (d, J=1.3 Hz, 1H), 4.84 (p, J=6.0 Hz, 1H), 3.73 (m, 1H), 3.46-3.36 (m, 1H), 3.26-3.15 (m, 1H), 2.90-2.79 (m, 1H), 2.76 (s, 3H), 2.47-2.20 (m, 2H), 1.34 (d, J=6.0 Hz, 3H), 1.19-1.09 (m, 2H), 1.06 (m, 2H) ppm; MS (ESI+) m/z 384 (M+H).

Provenance & Evidence