Cesium carbonate → HCID 68161654, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-[3-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-3-(2,2,2-trifluoro-ethyl)-urea (3.08 g, 8.3 mmol), 5-Ethynyl-1-methyl-1H-imidazole (1.78 g, 10 mmol) and cesium carbonate (5.43 g, 16.7 mmol) in dry DMSO (31 ml) was deoxygenated by evacuation /refill with N2 (×3). PdCl2(PCy3)2 (185 mg, 0.25 mmol) was added and the mixture was deoxygenated again (×3) then stirred and heated at 100° C. under N2 for 16 hours. The reaction was allowed to cool to RT, diluted with water (65 ml) and the mixture was extracted with EtOAc (3×50 ml). The combined organic extracts were washed with brine (40 ml) then dried (MgSO4), filtered and evaporated. The residue was mixed with dichloromethane (20 ml), cooled in ice and filtered to give the title compound (1.34 g, yellow solid). 1H NMR (400 MHz, Me-d3-OD): 8.59 (1H, d), 7.87-7.74 (4H, m), 7.50 (1H, t), 7.42 (1H, d), 7.37 (1H, s), 7.32 (1H, d), 7.10 (1H, dd), 3.95 (2H, q), 3.85 (3H, s). A solution of the title compound in methanol (10 ml) was cooled in ice and was treated with a solution of saturated hydrogen chloride in ethyl acetate (15 ml). The mixture was evaporated to give the bis-HCl salt (1.59 g, yellow foam). 1H NMR (400 MHz, Me-d3-OD): 9.06 (1H, s), 8.88 (1H, d), 8.34-8.27 (2H, m), 8.08 (2H, d), 7.65 (1H, d), 7.59 (1H, t), 7.47-7.35 (2H, m), 4.09 (3H, s), 3.96 (2H, q).

Provenance & Evidence