Nitrogen → (R)-4-((R)-1-((5-(4-(tert-butyl)thiazol-2-yl)-1-cyclopropyl-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), 2-bromo-4-(tert-butyl)thiazole (128.5 mg, 0.584 mmol), 1,2-dimethoxyethane (2 mL), 1 N Na2CO3 aqueous solution (0.73 mL, 0.73 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (14.0 mg, 0.012 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, 44.5 mg (yield 35.9%). 1H NMR (300 MHz, DMSO-d6) δ 8.16 (s, 1H), 7.65 (d, J=1.2 Hz, 1H), 7.61-7.58 (m, 1H), 7.59 (s, 1H), 7.35 (d, J=1.2 Hz, 1H), 4.81 (p, J=6.0 Hz, 1H), 3.77-3.65 (m, 1H), 3.45-3.35 (m, 1H), 3.25-3.14 (m, 1H), 2.89-2.74 (m, 1H), 2.41-2.20 (m, 2H), 1.35-1.29 (d, J=6 Hz, 3H), 1.16-1.08 (m, 2H), 1.08-0.98 (m, 2H) ppm; MS (ESI+) m/z 425.16 (M+H).

Provenance & Evidence