Technology Process of 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-6-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-3-pyridinyl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile
There total 18 articles about 3-chloro-5-{[6-chloro-2-fluoro-3-({5-[4-methyl-6-({[(4S)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]methyl}oxy)-3-pyridinyl]-1,3,4-oxadiazol-2-yl}methyl)phenyl]oxy}benzonitrile which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: 1,3-bis-(diphenylphosphino)propane; N-ethyl-N,N-diisopropylamine / palladium diacetate / dimethyl sulfoxide / 72 h / 75 °C / 3102.97 Torr / Inert atmosphere
2.1: hydrogenchloride; sodium nitrite / water / 16.5 h / -7 - 20 °C
2.2: pH 12
3.1: caesium carbonate / 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate / toluene / 22 h / 85 °C / Inert atmosphere
4.1: ethanol / 4 h / Reflux
5.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 2.5 h / 20 °C
5.2: 20 °C
With
hydrogenchloride; 1,3-bis-(diphenylphosphino)propane; caesium carbonate; N-ethyl-N,N-diisopropylamine; HATU; sodium nitrite;
1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate;
In
tetrahydrofuran; ethanol; water; dimethyl sulfoxide; toluene;
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: pyridinium p-toluenesulfonate / methanol; water / 5 h / Reflux
2.1: pyridine / 16.5 h / -10 - -5 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / acetone / 72 h / 20 °C
4.1: toluene-4-sulfonic acid; 2,2-dimethoxy-propane / toluene / 1 h / 50 °C
4.2: 2 h / 90 °C
5.1: caesium carbonate / 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate / toluene / 22 h / 85 °C / Inert atmosphere
6.1: ethanol / 4 h / Reflux
7.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 2.5 h / 20 °C
7.2: 20 °C
With
pyridine; pyridinium p-toluenesulfonate; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; HATU;
1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate;
In
tetrahydrofuran; methanol; ethanol; water; acetone; toluene;
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: pyridine / 16.5 h / -10 - -5 °C / Inert atmosphere
2.1: toluene-4-sulfonic acid / acetone / 72 h / 20 °C
3.1: toluene-4-sulfonic acid; 2,2-dimethoxy-propane / toluene / 1 h / 50 °C
3.2: 2 h / 90 °C
4.1: caesium carbonate / 1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate / toluene / 22 h / 85 °C / Inert atmosphere
5.1: ethanol / 4 h / Reflux
6.1: N-ethyl-N,N-diisopropylamine; HATU / tetrahydrofuran / 2.5 h / 20 °C
6.2: 20 °C
With
pyridine; caesium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; 2,2-dimethoxy-propane; HATU;
1,1'-binaphthalen-2-yl[bis(1,1-dimethylethyl)]phosphane; palladium diacetate;
In
tetrahydrofuran; ethanol; acetone; toluene;