Ethanol → HCID 58585903, compound

Participants

Reaction Steps

Sodium carbonate (21.2 mg, 0.000200 mol) in water (0.10 mL) was added to a mixture of (3S)-1-(5-bromopyridin-2-yl)-N-(4-hydroxycyclohexyl)piperidine-3-carboxamide (38.2 mg, 0.000100 mol, prepared as example 154), phenylboronic acid (14.6 mg, 0.000120 mol) and tetrakis(triphenylphosphine)palladium(0) (3.5 mg, 0.0000030 mol) in toluene (200.0 μL, 0.001878 mol) and ethanol (100.0 μL, 0.001713 mol). The resulting mixture was irradiated with microwaves at 150° C. for 20 min. Ethyl acetate (5 mL) was added and the mixture was washed with water and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DMF and purified by prep.-HPLC to give the desired product. LCMS: m/z 380.2 (M+H)+.

Provenance & Evidence