Dimethylformamide → HCID 59767790, compound

Participants

Reaction Conditions

Reaction Steps

A stream of nitrogen was passed through a solution of DMF (4 mL), N1-(1-cyanocyclopropyl)-4-fluoro-N2-{(1S)-2,2,2-trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl}-L-leucinamide described in step 3 of example 1 (150 mg), 1-(4-bromophenyl)-2,2,2-trifluoroethanol from step 1 in example 3 (92 mg) and 2 M Na2CO3 (750 μL) for 15 minutes followed by the addition of [1,1′-bis(diphenylphosphino)-ferrocene]dichloropalladium(II), complex (1:1) with dichloromethane (12 mg). The mixture was warmed to 80° C. for 3 hours under nitrogen. The mixture was cooled to room temperature, poured into ice (20 g) and saturated aqueous sodium bicarbonate (20 mL) and extracted with 50% ethyl acetate in diethyl ether (3×50 mL). The combined extracts were washed with brine and dried with magnesium sulfate. Removal of the solvent left a residue that was purified by chromatography on SiO2 using ethyl acetate and hexanes (20 to 50%) as eluent, followed by trituration using diethyl ether and hexanes to yield the title compound.

Provenance & Evidence