Technology Process of 2-[4-[2,3-Difluoro-4-(4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yl)phenoxy]butyl]-5-(8-methoxy-2-trifluoromethylimidazo[1,2-a]pyridin-5-yl)-4,4-dimethyl-2,4-dihydro-pyrazol-3-one
There total 10 articles about 2-[4-[2,3-Difluoro-4-(4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yl)phenoxy]butyl]-5-(8-methoxy-2-trifluoromethylimidazo[1,2-a]pyridin-5-yl)-4,4-dimethyl-2,4-dihydro-pyrazol-3-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: 2,2,6,6-tetramethyl-piperidine; n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere
1.2: 0.5 h / -78 °C
2.1: borane-THF / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere
2.2: 6 h / 60 °C
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
4.1: potassium carbonate / N,N-dimethyl-formamide; acetone / 5.5 h / 20 °C
5.1: boron trifluoride diethyl etherate / diethyl ether / 1 h / 20 °C / Inert atmosphere
6.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C
7.1: hydrazine hydrate / ethanol / 6 h / Reflux
8.1: aluminum (III) chloride / dichloromethane / 26 h / Reflux
9.1: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere
With
2,2,6,6-tetramethyl-piperidine; aluminum (III) chloride; n-butyllithium; borane-THF; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; potassium carbonate; hydrazine hydrate; triethylamine; potassium iodide;
In
tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmcl.2012.08.121
- Guidance literature:
-
Multi-step reaction with 7 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C
2: potassium carbonate / N,N-dimethyl-formamide; acetone / 5.5 h / 20 °C
3: boron trifluoride diethyl etherate / diethyl ether / 1 h / 20 °C / Inert atmosphere
4: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C
5: hydrazine hydrate / ethanol / 6 h / Reflux
6: aluminum (III) chloride / dichloromethane / 26 h / Reflux
7: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere
With
aluminum (III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; potassium carbonate; hydrazine hydrate; triethylamine; potassium iodide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmcl.2012.08.121
- Guidance literature:
-
Multi-step reaction with 5 steps
1: boron trifluoride diethyl etherate / diethyl ether / 1 h / 20 °C / Inert atmosphere
2: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C
3: hydrazine hydrate / ethanol / 6 h / Reflux
4: aluminum (III) chloride / dichloromethane / 26 h / Reflux
5: potassium carbonate; potassium iodide / N,N-dimethyl-formamide / 6 h / 60 °C / Inert atmosphere
With
aluminum (III) chloride; boron trifluoride diethyl etherate; sulfur trioxide pyridine complex; potassium carbonate; hydrazine hydrate; triethylamine; potassium iodide;
In
diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.bmcl.2012.08.121
