反应详情

A solution of (S)-tert-butyl 2-((S)-1-amino-1-oxo-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propan-2-ylcarbamoyl)piperidine-1-carboxylate (0.150 g) in dioxane (1 mL) was added to a stirred solution of 5-bromopicolinonitrile (0.055 g) and bis[bis(1,2-diphenylphosphino)ethane]palladium (0) (0.003 g) in dioxane (1 mL) under nitrogen. The resulting mixture was stirred for 10 min. A solution of potassium carbonate (0.124 g) in water (0.75 mL) was added and the resulting solution was stirred at 75° C. for 16 h. The cooled mixture was evaporated to dryness. The residue was taken up in ethyl acetate and washed with saturated brine, dried over sodium sulfate and adsorbed onto silica. The crude product was purified by flash silica chromatography, eluting with 3:1 ethyl acetate/isohexane). Pure fractions were evaporated to dryness to afford the subtitle compound (0.113 g).

1. stirringthe resulting solution was stirred at 75° C. for 16 h
2. customThe cooled mixture was evaporated to dryness
3. washwashed with saturated brine
4. dry with materialdried over sodium sulfate
5. customThe crude product was purified by flash silica chromatography
6. washeluting with 3:1 ethyl acetate/isohexane)
7. customPure fractions were evaporated to dryness