Nitrogen → (R)-4-((R)-1-((1-cyclopropyl-5-(2-methylthiazol-4-yl)-1H-benzo[d]imidazol-7-yl)oxy)ethyl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a microwave tube equipped with a stifling 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), 4-bromo-2-methylthiazole (103.9 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, 9.0 mg. 1H NMR (300 MHz, DMSO-d6) δ 8.94 (s, 1H), 8.13 (s, 1H), 7.59 (s, 1H), 7.41 (d, J=1.2 Hz, 1H), 7.14 (d, J=1.3 Hz, 1H), 4.74 (p, J=6.0 Hz, 1H), 3.72 (tt, J=7.2, 3.9 Hz, 1H), 3.45-3.35 (m, 1H), 3.23-3.14 (m, 1H), 2.82 (m, 1H), 2.60 (s, 3H), 2.43-2.19 (m, 2H), 1.32 (d, J=6.0 Hz, 3H), 1.11 (m, 2H), 1.08-0.98 (m, 2H) ppm; MS (ESI+) m/z 384.24 (M+H).

Provenance & Evidence