Technology Process of 1-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octane-4-carbaldehyde
There total 11 articles about 1-(4-(5-((5-cyclobutyl-1,3,4-oxadiazol-2-yl)amino)pyridin-2-yl)phenyl)-2-oxabicyclo[2.2.2]octane-4-carbaldehyde which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
With
sulfur trioxide pyridine complex; N-ethyl-N,N-diisopropylamine;
In
dichloromethane; dimethyl sulfoxide;
at 0 - 20 ℃;
for 2h;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 0.17 h / 20 °C / Inert atmosphere
1.2: 1 h / 100 °C / Inert atmosphere; Sealed tube
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C
3.1: N-Bromosuccinimide / dichloromethane; tetrahydrofuran / -78 - 20 °C
4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene; tetrahydrofuran / 3 h / 40 - 100 °C / Inert atmosphere
5.1: dichloromethane; tetrahydrofuran / 1 h / 20 °C
5.2: 1 h / 20 °C
5.3: 16 h / 20 °C
6.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C
With
N-Bromosuccinimide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; potassium carbonate; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; toluene;
1.1: |Suzuki Coupling;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 0.53 h / -78 - 20 °C / Inert atmosphere
1.2: 2 h / 20 °C
2.1: potassium carbonate; tetrakis(triphenylphosphine) palladium(0) / water; 1,4-dioxane / 0.17 h / 20 °C / Inert atmosphere
2.2: 1 h / 100 °C / Inert atmosphere; Sealed tube
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C
4.1: N-Bromosuccinimide / dichloromethane; tetrahydrofuran / -78 - 20 °C
5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene; tetrahydrofuran / 3 h / 40 - 100 °C / Inert atmosphere
6.1: dichloromethane; tetrahydrofuran / 1 h / 20 °C
6.2: 1 h / 20 °C
6.3: 16 h / 20 °C
7.1: N-ethyl-N,N-diisopropylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 2 h / 0 - 20 °C
With
N-Bromosuccinimide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; potassium carbonate; diisopropylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; dimethyl sulfoxide; toluene;
2.1: |Suzuki Coupling;