Technology Process of sodium 3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl sulfate
There total 23 articles about sodium 3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl sulfate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
3-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dihydro-1-(3-hydroxy-4-methoxyphenyl)-8-methoxy-4-oxo-[1]benzopyrano[3,4-b]pyrrol-7-yl 2,2,2-trichloroethyl sulfate;
With
ammonium formate; zinc;
In
tetrahydrofuran; methanol;
at 20 ℃;
for 15h;
In
methanol; water; ethyl acetate;
DOI:10.1016/j.bmc.2011.10.030
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: potassium carbonate / acetone / 9 h / Inert atmosphere; Reflux
2.1: tert.-butyl lithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: 2 h / -78 - 20 °C
2.3: pH 3
3.1: dichloromethane / 26 h / 20 °C
4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere
5.1: potassium hydroxide / ethanol; water / 2 h / Reflux
6.1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Reflux
7.1: quinoline; copper(II) oxide / 0.17 h / 220 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 19 h / 20 °C
9.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
10.1: hydrogenchloride / methanol / 12 h / 30 °C
11.1: ammonium formate; zinc / tetrahydrofuran; methanol / 15 h / 20 °C
11.2: Amberlite IRC-50 (Na+ form)
With
quinoline; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; hydrogen; tert.-butyl lithium; ammonium formate; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; triethylamine; copper(II) oxide; potassium hydroxide; zinc;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone;
4.1: Suzuki-Miyaura coupling;
DOI:10.1016/j.bmc.2011.10.030
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere
2.1: hydrogenchloride / methanol / 3 h / 20 °C
3.1: toluene-4-sulfonic acid / dichloromethane / 3.5 h / Reflux
4.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / tetrahydrofuran; water / 3 h / Reflux; Inert atmosphere
5.1: potassium hydroxide / ethanol; water / 2 h / Reflux
6.1: pyridinium p-toluenesulfonate / dichloromethane / 8 h / Reflux
7.1: quinoline; copper(II) oxide / 0.17 h / 220 °C / Inert atmosphere
8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 19 h / 20 °C
9.1: dmap; triethylamine / dichloromethane / 10 h / 0 - 20 °C / Inert atmosphere
10.1: hydrogenchloride / methanol / 12 h / 30 °C
11.1: ammonium formate; zinc / tetrahydrofuran; methanol / 15 h / 20 °C
11.2: Amberlite IRC-50 (Na+ form)
With
quinoline; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium(0); palladium 10% on activated carbon; hydrogen; ammonium formate; pyridinium p-toluenesulfonate; sodium carbonate; toluene-4-sulfonic acid; triethylamine; copper(II) oxide; potassium hydroxide; zinc;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; ethyl acetate;
1.1: Suzuki-Miyaura coupling / 4.1: Suzuki-Miyaura coupling;
DOI:10.1016/j.bmc.2011.10.030