Potassium Carbonate → N-(2',4'-difluoro-5-(5-(2-oxopyrrolidin-1-yl)-1H-benzo[d]imidazol-1-yl)-[1,1'-biphenyl]-3-yl)cyclopropanesulfonamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(5-(5-bromo-1H-benzo[d]imidazol-1-yl)-2′,4′-difluoro-[1,1′-biphenyl]-3-yl)cyclopropanesulfonamide (50 mg, 0.099 mmol, 1 eq.) in DMSO (2 ml) was degassed by nitrogen bubbling for 10 min. Copper(I)iodide (11.3 mg, 0.059 mmol, 0.6 eq.), K2CO3 (42 mg, 0.298 mmol, 3 eq.), N,N-dimethyl glycine HCl (11 mg, 0.079 mmol) and 2-pyrrolidone (42 mg, 0.49 mmol, 5 eq.) were added and the mixture was further degassed for 10 min and then heated to 110° C. for 16 h. The mixture was cooled to RT and diluted with ethyl acetate, filtered through a celite bed and washed with water and brine solution. The ethyl acetate layer was dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to afford the product in 90% yield (45 mg). 1H NMR (400 MHz, DMSO-d6): δ 8.65 (s, 1H), 7.96 (d, 1H), 7.78-7.65 (m, 3H), 7.54 (m, 2H), 7.45-7.42 (m, 2H), 7.28-7.24 (dt, 1H), 3.9 (t, 2H), 2.88-2.8 (m, 1H), 2.12-2.02 (m, 2H), 1.0 (m, 4H): LC-MS (ESI): Calculated mass: 508.54; Observed mass: 508.7 [M+H]+ (rt: 1.46 min).

Provenance & Evidence