反应详情

温度

100 °C

To a stirred solution of ethyl (3S)-3-[4-[(2-bromo-[1,2,4]triazolo[1,5-a]pyridin-6-yl)methoxy]phenyl]hex-4-ynoate (0.3 g, 0.67 mmol) and 4-isopropyl-phenylboronic acid (0.24 g, 1.0 mmol) in toluene (16 mL) and EtOH (4 mL) is added 2 M K2CO3 (0.6 mL, 1.34 mmol). The mixture is purged with argon for 30 minutes. Pd(PPh3)4 (0.077 g, 0.067 mmol) is added and the mixture is heated at 100° C. overnight. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth. The filtrate is diluted with water (30 mL) and extracted with EtOAc (2×20 mL). The combined organic extracts are washed with saturated brine solution (20 mL), dried over sodium sulphate, filtered, and concentrated to dryness. The crude material is purified by silica gel chromatography (combiflash using 24 g redisep column) eluting with 45% EtOAc/hexane to give the title compound as a brown liquid (0.22 g, 68.75%). LCMS m/z 481 (M+H)+.

1. customThe mixture is purged with argon for 30 minutes
2. temperatureThe reaction mixture is cooled to room temperature
3. filtrationfiltered through diatomaceous earth
4. additionThe filtrate is diluted with water (30 mL)
5. extractionextracted with EtOAc (2×20 mL)
6. washThe combined organic extracts are washed with saturated brine solution (20 mL)
7. dry with materialdried over sodium sulphate
8. filtrationfiltered
9. concentrationconcentrated to dryness
10. customThe crude material is purified by silica gel chromatography (combiflash using 24 g redisep column)
11. washeluting with 45% EtOAc/hexane