Technology Process of benzyl [7,8-dimethoxy-5-((trimethylsilyl)ethynyl)quinolin-4-yl]carbonate
There total 8 articles about benzyl [7,8-dimethoxy-5-((trimethylsilyl)ethynyl)quinolin-4-yl]carbonate which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
benzyl (5-bromo-7,8-dimethoxyquinolin-4-yl)carbonate; trimethylsilylacetylene;
With
bis-triphenylphosphine-palladium(II) chloride; triethylamine;
In
N,N-dimethyl-formamide;
at 20 ℃;
for 0.25h;
Inert atmosphere;
With
copper(l) iodide;
In
N,N-dimethyl-formamide;
at 70 ℃;
for 12h;
Inert atmosphere;
DOI:10.1021/jo3020598
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 2 h / Reflux
1.2: 3 h / 100 °C
2.1: diphenylether / 0.17 h / 260 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 70 °C
3.2: 24 h / 20 °C
4.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere
4.2: 12 h / 70 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; sodium hydride; triethylamine;
In
tetrahydrofuran; diphenylether; N,N-dimethyl-formamide; mineral oil;
4.1: |Sonogashira Cross-Coupling / 4.2: |Sonogashira Cross-Coupling;
DOI:10.1021/jo3020598
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: acetic acid; bromine / 24 h / 20 °C
2.1: potassium carbonate / acetone / 55 °C
3.1: sodium hydroxide / methanol; water / 2 h / 65 °C
3.2: pH < 2
4.1: diphenyl phosphoryl azide; triethylamine / tetrahydrofuran / 2 h / 65 °C
5.1: potassium hydroxide / ethanol / 15 h / 78 °C
6.1: 2 h / Reflux
6.2: 3 h / 100 °C
7.1: diphenylether / 0.17 h / 260 °C
8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 - 70 °C
8.2: 24 h / 20 °C
9.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere
9.2: 12 h / 70 °C / Inert atmosphere
With
bis-triphenylphosphine-palladium(II) chloride; diphenyl phosphoryl azide; bromine; sodium hydride; potassium carbonate; acetic acid; triethylamine; potassium hydroxide; sodium hydroxide;
In
tetrahydrofuran; methanol; diphenylether; ethanol; water; N,N-dimethyl-formamide; acetone; mineral oil;
4.1: |Curtius Rearrangement / 9.1: |Sonogashira Cross-Coupling / 9.2: |Sonogashira Cross-Coupling;
DOI:10.1021/jo3020598
