Technology Process of 5-fluoro-6-chloro-2-[(6-oxo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-3-yl)methyl]benzonitrile
There total 12 articles about 5-fluoro-6-chloro-2-[(6-oxo-7-{[2-(trimethylsilyl)ethoxy]methoxy}-6,7,8,9-tetrahydro-3H-pyrrolo[2,3-c][1,7]naphthyridin-3-yl)methyl]benzonitrile 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:
-
Multi-step reaction with 10 steps
1.1: tetrabutylammomium bromide; sodium hydroxide / water; toluene / 0.75 h
2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 2 h / Reflux
3.1: sodium hydride / N,N-dimethyl-formamide / -20 - -10 °C
4.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere
5.1: triethylamine / dichloromethane / 0 °C
6.1: tris-(dibenzylideneacetone)dipalladium(0); N-Methyldicyclohexylamine; lithium chloride; tri tert-butylphosphoniumtetrafluoroborate / 1,4-dioxane / 16 h / 80 °C / Inert atmosphere
7.1: sodium ethanolate / ethanol / 8 h / 20 °C
8.1: toluene-4-sulfonic acid / 1,4-dioxane / 5.5 h / 5.5 °C
9.1: sodium cyanoborohydride; acetic acid / 2 h / 20 °C
10.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Cooling with ice
10.2: 1 h
With
tris-(dibenzylideneacetone)dipalladium(0); N-Bromosuccinimide; N-Methyldicyclohexylamine; tetrabutylammomium bromide; sodium ethanolate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; triethylamine; lithium chloride; sodium hydroxide; lithium hexamethyldisilazane; tri tert-butylphosphoniumtetrafluoroborate; dibenzoyl peroxide;
In
tetrahydrofuran; 1,4-dioxane; tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1021/jm200208d
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: methylhydrazine / diethyl ether / 0 - 20 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / 1,4-dioxane / 5.5 h / 5.5 °C
3.1: sodium cyanoborohydride; acetic acid / 2 h / 20 °C
4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Cooling with ice
4.2: 1 h
With
sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; methylhydrazine;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; mineral oil;
DOI:10.1021/jm200208d
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: toluene-4-sulfonic acid / 1,4-dioxane / 5.5 h / 5.5 °C
2.1: sodium cyanoborohydride; acetic acid / 2 h / 20 °C
3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / Cooling with ice
3.2: 1 h
With
sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid;
In
tetrahydrofuran; 1,4-dioxane; mineral oil;
DOI:10.1021/jm200208d
