Nitrogen → (R)-4-((R)-1-((3-cyclopropyl-6-(5-methylthiophen-2-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a microwave tube equipped with a stirring bar, (R)-4-((R)-1-((6-bromo-3-cyclopropyl-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one: (100 mg, 0.274 mmol), (5-methylthiophen-2-yl)boronic acid (70.0 mg, 0.493 mmol), 1,2-dimethoxyethane (1.1 mL), 1 N Na2CO3 aqueous solution (0.55 mL, 0.55 mmol) were added, the mixture was bubbled N2 for 5 minutes before Pd(PPh3)4 (31.6 mg, 0.027 mmol) was added. The tube was sealed and heated in a microwave at 150° C. for 20 minutes. 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, 57.2 mg (yield 54.6%). 1H NMR (300 MHz, DMSO-d6) δ 8.25 (s, 1H), 7.63 (s, 1H), 7.56 (broad s, 1H), 7.48 (d, J=3.6 Hz, 1H), 6.78 (dm, J=3.6 Hz, 1H), 5.50-5.36 (m, 1H), 3.71-3.61 (m, 1H), 3.46-3.36 (m, 1H), 3.24-3.15 (m, 1H), 2.91-2.76 (m, 1H), 2.45 (s, 3H), 2.36-2.28 (m, 2H), 1.41 (d, J=6.2 Hz, 3H), 1.15-1.09 (m, 2H), 1.08-1.01 (m, 2H) ppm; MS (ESI+) m/z 383 (M+H).

Provenance & Evidence