Technology Process of tert-butyl 4-(3,4-dichlorophenyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate
There total 11 articles about tert-butyl 4-(3,4-dichlorophenyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydroisoquinoline-2(1H)-carboxylate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
triethylamine;
dmap;
In
dichloromethane;
at 20 ℃;
for 4h;
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: sodium tetrahydroborate / methanol / 2 h / 0 °C
2.1: sulfuric acid / dichloromethane; water / 28 h / 0 °C
2.2: pH ~ 9
3.1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
4.1: hydrogen bromide / water; acetic acid / 8 h / Reflux
5.1: pyridine / dichloromethane / 1 h / -78 - 0 °C
6.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere
7.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.92 h / 0 °C / Reflux
8.1: methanol / 1 h / Reflux
9.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C
With
pyridine; methanol; dmap; sodium tetrahydroborate; sulfuric acid; hydrogen bromide; potassium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; diethylamine; isopropyl alcohol;
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: sulfuric acid / dichloromethane; water / 28 h / 0 °C
1.2: pH ~ 9
2.1: Chiralpak AD column / diethylamine; isopropyl alcohol / Resolution of racemate
3.1: hydrogen bromide / water; acetic acid / 8 h / Reflux
4.1: pyridine / dichloromethane / 1 h / -78 - 0 °C
5.1: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dimethyl sulfoxide / 1 h / 80 °C / Inert atmosphere
6.1: N,N,N',N'-tetramethyl-1,8-diaminonaphthalene / dichloromethane / 0.92 h / 0 °C / Reflux
7.1: methanol / 1 h / Reflux
8.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C
With
pyridine; methanol; dmap; sulfuric acid; hydrogen bromide; potassium acetate; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; triethylamine;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
dichloromethane; water; acetic acid; dimethyl sulfoxide; diethylamine; isopropyl alcohol;