Potassium Carbonate → HCID 10323257, compound

Participants

Reaction Conditions

Reaction Steps

(2S)-N-(cyanomethyl)-4-methyl-2-({(R)-phenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}oxy)pentanamide (100 mg, 0.216 mmol), 4-(4-bromophenyl)pyridine (56 mg, 0.238 mmol) and 2M K2CO3 (324 ul, 0.648 mmol) were dissolved in 1.6 ml DMF and the solution was degassed 3 times. PdCl2(dppf) (4.8 mg, 0.03 mmol) was added and the mixture was stirred overnight at 80° C. The solution was cooled, poured into 8 ml NaHCO3 (sat.) and extracted 3 times with 2 ml ethyl acetate. The combined organic layers were then washed with 4× water, then dried with Na2SO4. (2S)-N-(cyanomethyl)-4-methyl-2-{[(R)-phenyl(4′-pyridin-4-yl-1,1′-biphenyl-4-yl)methyl]oxy}pentanamide was obtained after purification on silica gel (2% MeOH/38% ethyl acetate/60% hexanes).

Provenance & Evidence