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N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,4,5-trimethoxyaniline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In dichloromethane;
Example 106 N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoyl]-3,4,5-trimethoxyaniline 3,4,5-Trimethoxyaniline (0.216 g, 1.18 mmol), triethylamine (0.119 g, 1.18 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.199 g, 1.18 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-acetoxybenzoic acid (0.200 g, 0.535 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform: methanol = 10:1) to obtain the titled compound (0.109 g, 0.202 mmol, 38percent).
N-[5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(pyridin-3-ylmethyloxy)benzoyl]-3,4,5-trimethoxyaniline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With triethylamine; In dichloromethane;
Example 128 N-[5-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoyl]-3,4,5-trimethoxyaniline 3,4,5-Trimethoxyaniline (0.260 g, 1.42 mmol), triethylamine (0.144 g, 1.42 mmol) and <strong>[37091-73-9]2-chloro-1,3-dimethylimidazolinium chloride</strong> (0.240 g, 1.42 mmol) were added to a methylene chloride solution (20 ml) of 5-(5,6-dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridylmethyloxy)benzoic acid (0.200 g, 0.473 mmol) and the resulting solution was stirred at room temperature for 12 hours. The reaction solution was poured into ice water and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by preparative thin-layer chromatography (chloroform: methanol = 10:1) and then recrystallized from ether to obtain the titled compound (0.050 g, 0.085 mmol, 18percent).
5-Bromo-2-methyl-3-((3,4,5-trimethoxyphenyl)selenyl)-1H-indole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
41%
General procedure: Similar to the reported method [19], a mixture of the appropriate indole (0.6 mmol), 1,2-bis-(3,4,5-trimethoxyphenyl)diselenide(0.35 mmol, 0.45 g mixture of 1,2-bis-(3,4,5-trimethoxyphenyl)diselenide with 1,10-selenobis(3,4,5-trimethoxybenzene)), FeCl3 (20 molpercent) and I2 (1 molpercent, 0.0001 g/mL in CH3CN) was placed into the microwave cavity (closed vessel mode). Microwave irradiation at 150 W was used, the temperature being ramped from 25 °C to 80 °C. Once 80 °C was reached, takingabout 1 min, the reaction mixture was held at this temperature for 30 min while stirring, until complete consumption of the starting material, as monitored by TLC. After the evaporation of the solvent,the residual crude product was purified by column chromatography on silica gel (200-300 mesh) with petroleumether/AcOEt (v/v 5:1) or pure CH2Cl2.
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