Technology Process of tert-butyl-{4-[4-(3-{[(2,5-difluorophenyl)sulfonyl](methoxymethyl)amino}-2-fluorophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]pyridin-2-yl}carbamate
There total 12 articles about tert-butyl-{4-[4-(3-{[(2,5-difluorophenyl)sulfonyl](methoxymethyl)amino}-2-fluorophenyl)-2-(tetrahydro-2H-pyran-4-yl)-1,3-thiazol-5-yl]pyridin-2-yl}carbamate which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
palladium diacetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
2-methyl-propan-1-ol;
at 120 ℃;
for 0.5h;
Microwave irradiation;
DOI:10.1002/cmdc.201402424
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
3.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C
3.2: 0.33 h / 0 °C
4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane; tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4.2: 0 °C
5.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1.08 h / -78 °C / Inert atmosphere
5.2: 1.17 h / -78 - 0 °C
6.1: pyridinium perbromide hydrobromide / N,N-dimethyl-formamide / 0.83 h / 20 °C / Inert atmosphere
6.2: 2 h / 60 °C
7.1: caesium carbonate / palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere
With
4-methyl-morpholine; pyridine; dmap; n-butyllithium; pyridinium perbromide hydrobromide; isopropylmagnesium chloride; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine;
palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
7.1: Buckhwald-Hartwig reaction;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: pyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere
2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 0 - 20 °C
3.1: isopropylmagnesium chloride / tetrahydrofuran / 0 - 20 °C
3.2: 0.33 h / 0 °C
4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / dichloromethane; tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4.2: 0 °C
5.1: N-ethyl-N,N-diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1.08 h / -78 °C / Inert atmosphere
5.2: 1.17 h / -78 - 0 °C
6.1: pyridinium perbromide hydrobromide / N,N-dimethyl-formamide / 0.83 h / 20 °C / Inert atmosphere
6.2: 2 h / 60 °C
7.1: caesium carbonate / palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene / tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere
With
4-methyl-morpholine; pyridine; dmap; n-butyllithium; pyridinium perbromide hydrobromide; isopropylmagnesium chloride; caesium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine;
palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;
In
tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
7.1: Buckhwald-Hartwig reaction;