Technology Process of 4-tert-butyl-2-({2-[4-chloro-1'-neopentyl-7-hydroxy-1,2-dihydrospiro[indole-3,4'-piperidine]-1-yl]phenyl}amino)-1,3-thiazole-5-carbonitrile
There total 12 articles about 4-tert-butyl-2-({2-[4-chloro-1'-neopentyl-7-hydroxy-1,2-dihydrospiro[indole-3,4'-piperidine]-1-yl]phenyl}amino)-1,3-thiazole-5-carbonitrile which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
4-tert-butyl-2-(2-(4-chloro-7-methoxy-1'-neopentylspiro[indoline-3,4'-piperidine]-1-yl)phenylamino)thiazole-5-carbonitrile;
With
boron trichloride; tetra-(n-butyl)ammonium iodide;
In
dichloromethane;
at -50 - 23 ℃;
for 19h;
Inert atmosphere;
With
methanol;
In
dichloromethane;
for 0.5h;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: triethylamine / 1,2-dichloro-ethane / 4 h / 23 °C
2.1: Dess-Martin periodane / 0 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 1 h / 0 °C
3.2: 1.5 h / 0 °C
4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 16 h / -78 - 20 °C
5.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 18 h / 110 °C / Microwave irradiation; Inert atmosphere
6.1: sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 18 h / 110 °C / Inert atmosphere
7.1: tetra-(n-butyl)ammonium iodide; boron trichloride / dichloromethane / 19 h / -50 - 23 °C / Inert atmosphere
7.2: 0.5 h
With
hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); boron trichloride; tetra-(n-butyl)ammonium iodide; sodium carbonate; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; toluene;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate; ethanol / tetrahydrofuran / 0 - 20 °C
2.1: Dess-Martin periodane / 0 - 20 °C / Inert atmosphere
3.1: hydrogenchloride / dichloromethane; water; 1,4-dioxane / 1 h / 0 °C
3.2: 1.5 h / 0 °C
4.1: sodium bis(2-methoxyethoxy)aluminium dihydride / dichloromethane / 16 h / -78 - 20 °C
5.1: caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 18 h / 110 °C / Microwave irradiation; Inert atmosphere
6.1: sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) / toluene / 18 h / 110 °C / Inert atmosphere
7.1: tetra-(n-butyl)ammonium iodide; boron trichloride / dichloromethane / 19 h / -50 - 23 °C / Inert atmosphere
7.2: 0.5 h
With
hydrogenchloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium(0); ethanol; boron trichloride; tetra-(n-butyl)ammonium iodide; sodium carbonate; caesium carbonate; Dess-Martin periodane; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium bis(2-methoxyethoxy)aluminium dihydride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;