反应详情

温度

50 °C

Tetrakis(triphenylphosphine)palladium(0) (16.0 mg) was added to a mixture of (2-chlorophenyl)boronic acid (76.0 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenyl trifluoromethanesulfonate (100 mg) and sodium carbonate (51.4 mg) in EtOH (3 mL), water (1.5 mL) and DMF (dry) (2 mL). The mixture was stirred at 50° C. under nitrogen for 19 hr. Silica-gel was added and the volatiles were removed in vacuo. The mixture supported on silica-gel was purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc), dissolved in MeCN/DMSO (4700/300 μM) and purified by preparative HPLC (C18, eluted with water in acetonitrile containing 0.1% TFA). The desired fractions were neutralized with sat.NaHCO3 aq., extracted with EtOAc and washed with brine. The organic layer was separated, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was crystallized from MeCN-THF/hexane to give the title compound (38.4 mg) as colorless crystals.

1. additionSilica-gel was added
2. customthe volatiles were removed in vacuo
3. customwas purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc)
4. dissolutiondissolved in MeCN/DMSO (4700/300 μM)
5. custompurified by preparative HPLC (C18, eluted with water in acetonitrile containing 0.1% TFA)
6. extractionNaHCO3 aq., extracted with EtOAc
7. washwashed with brine
8. customThe organic layer was separated
9. dry with materialdried over anhydrous magnesium sulfate
10. concentrationconcentrated in vacuo
11. customThe residue was crystallized from MeCN-THF/hexane