Technology Process of (3-(2-(2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethoxy)ethoxy)-1,1-difluoropropyl)phosphonic acid
There total 12 articles about (3-(2-(2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethoxy)ethoxy)-1,1-difluoropropyl)phosphonic acid which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
diethyl 3-(2-(2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethoxy)ethoxy)-1,1-difluoropropylphosphonate;
With
trimethylsilyl bromide;
In
dichloromethane;
at 0 - 22 ℃;
for 19h;
With
ammonium acetate; water;
In
acetonitrile;
DOI:10.1021/acs.jmedchem.6b00489
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: triethylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 60 °C / Inert atmosphere
2.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / butan-1-ol; water / 100 °C / Inert atmosphere
3.1: hydrogen / palladium 10% on activated carbon / dichloromethane; ethanol / 20 °C
4.1: boron tribromide / dichloromethane / 0.5 h / Cooling with ice water
5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 22 °C
5.2: 18 h
6.1: trimethylsilyl bromide / dichloromethane / 19 h / 0 - 22 °C
With
potassium phosphate; trimethylsilyl bromide; hydrogen; boron tribromide; sodium hydride; triethylamine;
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis-triphenylphosphine-palladium(II) chloride; tris-(dibenzylideneacetone)dipalladium(0); copper(l) iodide; palladium 10% on activated carbon;
In
ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; butan-1-ol;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere
1.2: 20 °C
2.1: sodium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 100 °C / Inert atmosphere
3.1: potassium phosphate / tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / butan-1-ol; water / 100 °C / Inert atmosphere
4.1: hydrogen / palladium 10% on activated carbon / dichloromethane; ethanol / 20 °C
5.1: boron tribromide / dichloromethane / 0.5 h / Cooling with ice water
6.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 22 °C
6.2: 18 h
7.1: trimethylsilyl bromide / dichloromethane / 19 h / 0 - 22 °C
With
potassium phosphate; trimethylsilyl bromide; hydrogen; sodium acetate; sodium hexamethyldisilazane; boron tribromide; sodium hydride;
dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tris-(dibenzylideneacetone)dipalladium(0); palladium 10% on activated carbon;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; mineral oil; butan-1-ol;