Dichloromethane → HCID 58869054, compound

Participants

Reaction Conditions

Reaction Steps

N2-[(1S)-1-(4-bromophenyl)-2,2-difluoroethyl]-N1-(1-cyanocyclopropyl)-4-fluoro-L-leucinamide (11.2 g, 25.9 mmol), 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]cyclopropanecarboxamide (8.2 g, 28.5 mmol, 1:1 equiv) and 2M sodium carbonate solution (35.4 mL, 70.8 mmol, 2.7 equiv) were mixed in 225 mL N,N-dimethylformamide. The mixture was degassed 3 times with nitrogen, then [1,1′-bis(diphenylphosphino)ferrocene]palladium (II) chloride, 1:1 complex with dichloromethane (838 mg, 1.15 mmol, 0.044 equiv) was added and mixture degassed again 3 times with nitrogen, heated at 80° C. for 6 hours. The reaction mixture was poured into H2O (900 mL), extracted with ethyl acetate (2×250 mL) and dichloromethane (250 mL). Combined organic fractions were washed with brine, dried over sodium sulphate and evaporated. The residue was purified by flash chromatography, eluting first with 1:1 ethyl acetate/hexane, then with 9:1 ethyl acetate/dichloromethane. The light pink recovered solid was stirred in 150 mL of 1:1 ethyl acetate/dichloromethane for 2 hours and filtered to yield the title compound.

Provenance & Evidence