反应详情

温度

115 °C

A “Personal Chemistry” microwave vial was charged with the title compound of Example 2 (107.1 mg, 0.3 mmol), 3,4,5-trimethoxyaniline (219.9 mg, 1.2 mmol), palladium (II) acetate (3.4 mg, 5 mol %), 1,1′-bis(diphenylphosphino)ferrocene (16.6 mg, 10 mol %), and sodium tert-butoxide (57.7 mg, 0.6 mmol). The reagents were suspended in toluene (2 mL) and were heated with microwave radiation to a temperature of 115° C. for fifteen minutes. After allowing the reaction vessel to cool, the suspension was filtered and the filtrate evaporated. The residue was purified by flash chromatography, and hydrolysis was performed by dissolving the product in 25% dimethylsulfoxide/ethanol, adding 5 drops of 1 N sodium hydroxide and 5 drops of 30% aqueous hydrogen peroxide, followed by stirring at room temperature for 3 hours. The DMSO/ethanol mixture was then diluted with water and extracted into EtOAc (3×). The combined organics were washed with brine (2×), dried over Na2SO4, and concentrated. The compound was purified by column chromatography (hexane/EtOAc) to yield 28.4 mg (20%) of the title compound as a yellow powder. LCMS m/z: (M+H) 478.3

1. temperatureto cool
2. filtrationthe suspension was filtered
3. customthe filtrate evaporated
4. customThe residue was purified by flash chromatography, and hydrolysis
5. dissolutionby dissolving the product in 25% dimethylsulfoxide/ethanol
6. additionadding 5 drops of 1 N sodium hydroxide and 5 drops of 30% aqueous hydrogen peroxide
7. additionThe DMSO/ethanol mixture was then diluted with water
8. extractionextracted into EtOAc (3×)
9. washThe combined organics were washed with brine (2×)
10. dry with materialdried over Na2SO4
11. concentrationconcentrated
12. customThe compound was purified by column chromatography (hexane/EtOAc)