反应详情

温度

100 °C

A mixture of 4-(5-bromo-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino)-benzoic acid ethyl ester (2) (380 mg; 1.1 mmol), 4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-benzamide (5) (510 mg; 1.3 mmol), tetrakis(triphenylphosphine)palladium (130 mg; 0.1 mmol), 1N sodium carbonate (1.6 mL; 3.2 mmol), and 1,2-dimethoxyethane (8 mL) was heated at 100° C. in a sealed pressure vessel for 16 h. The mixture was cooled to room temperature, treated with water (70 mL) and extracted with ethyl acetate (3×60 mL). The combined organic extracts were washed with water (1×40 mL) and brine (1×40 mL), dried over sodium sulfate and concentrated in vacuo. The crude residue was purified by flash chromatography (3:1-1:3, hexane/EtOAc, gradient) to give 4-{5-[3-(4-tert-butyl-benzoylamino)-2-methylphenyl]-1-methyl-2-oxo-1,2-dihydropyridin-3-ylamino}-benzoic acid ethyl ester (6) as a brown solid (460 mg).

1. temperatureThe mixture was cooled to room temperature
2. extractionextracted with ethyl acetate (3×60 mL)
3. washThe combined organic extracts were washed with water (1×40 mL) and brine (1×40 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuo
6. customThe crude residue was purified by flash chromatography (3:1-1:3, hexane/EtOAc, gradient)