Technology Process of 3-[6-(2,4-difluoro-phenylamino)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-N-(tetrahydro-pyran-4-yl)-benzamide
There total 10 articles about 3-[6-(2,4-difluoro-phenylamino)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-methoxy-N-(tetrahydro-pyran-4-yl)-benzamide which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: 79 percent / CrO3; aq. H2SO4 / acetone
2.1: 70 percent / hydrazine hydrate / ethanol; butan-1-ol / 1 h / Heating
3.1: KN(TMS)2 / tetrahydrofuran / -78 °C
4.1: n-BuLi / tetrahydrofuran
4.2: 63 percent / tetrahydrofuran
5.1: 96 percent / PPh3; NaOtBu; R-(+)-BINAP / Pd(OAc)2 / dioxane / 0.25 h / Heating
6.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.17 h / Heating
7.1: hydrochloric acid / ethanol / 0.25 h
With
chromium(VI) oxide; hydrogenchloride; n-butyllithium; sulfuric acid; potassium hexamethylsilazane; hydrazine hydrate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; 1,1'-carbonyldiimidazole; sodium t-butanolate;
palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; acetone; butan-1-ol;
1.1: Jones oxidation / 5.1: Buchwald reaction;
DOI:10.1016/j.bmcl.2005.10.015
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: 70 percent / hydrazine hydrate / ethanol; butan-1-ol / 1 h / Heating
2.1: KN(TMS)2 / tetrahydrofuran / -78 °C
3.1: n-BuLi / tetrahydrofuran
3.2: 63 percent / tetrahydrofuran
4.1: 96 percent / PPh3; NaOtBu; R-(+)-BINAP / Pd(OAc)2 / dioxane / 0.25 h / Heating
5.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.17 h / Heating
6.1: hydrochloric acid / ethanol / 0.25 h
With
hydrogenchloride; n-butyllithium; potassium hexamethylsilazane; hydrazine hydrate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; 1,1'-carbonyldiimidazole; sodium t-butanolate;
palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; ethanol; butan-1-ol;
4.1: Buchwald reaction;
DOI:10.1016/j.bmcl.2005.10.015
- Guidance literature:
-
Multi-step reaction with 5 steps
1.1: KN(TMS)2 / tetrahydrofuran / -78 °C
2.1: n-BuLi / tetrahydrofuran
2.2: 63 percent / tetrahydrofuran
3.1: 96 percent / PPh3; NaOtBu; R-(+)-BINAP / Pd(OAc)2 / dioxane / 0.25 h / Heating
4.1: 1,1'-carbonyldiimidazole / tetrahydrofuran / 0.17 h / Heating
5.1: hydrochloric acid / ethanol / 0.25 h
With
hydrogenchloride; n-butyllithium; potassium hexamethylsilazane; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; triphenylphosphine; 1,1'-carbonyldiimidazole; sodium t-butanolate;
palladium diacetate;
In
tetrahydrofuran; 1,4-dioxane; ethanol;
3.1: Buchwald reaction;
DOI:10.1016/j.bmcl.2005.10.015
