Product Name

Synthetic route

(Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-75-7

(Ε)-6-nitro-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
With sodiumsulfide nonahydrate In methanol at 65℃; for 3h; Temperature;94.38%
With iron; ammonium chloride In ethanol; water at 50℃; for 2 - 8h;91.8%
With iron; ammonium chloride In ethanol; water at 50℃; for 2 - 8h;91.8%
6-nitroindazole
7597-18-4

6-nitroindazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium carbonate; iodine / N,N-dimethyl-formamide / 25 °C
2: methanesulfonic acid / dichloromethane; tetrahydrofuran / 5 h / 25 °C
3: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 100 °C
4: ammonium chloride; iron / ethanol; water / 2 h / 50 °C
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate; iodine / N,N-dimethyl-formamide / 25 - 60 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 60 °C
3.1: potassium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 8 h / 60 - 100 °C / Inert atmosphere
3.2: 60 °C
4.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
5.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
View Scheme
Multi-step reaction with 4 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 2 h / 82 °C
2.1: sodium hydroxide; iodine / N,N-dimethyl-formamide / 14 h / 10 - 25 °C
2.2: 0.5 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
4.1: ammonium chloride; iron / water; ethanol / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1: iodine; potassium carbonate
2: methanesulfonic acid
3: N-ethyl-N,N-diisopropylamine; palladium diacetate; tris-(o-tolyl)phosphine
4: iron; ammonium chloride
View Scheme
Multi-step reaction with 4 steps
1.1: trichlorophosphate / 5 h / 60 - 102 °C
2.1: methanesulfonic acid / dichloromethane / 6 h / 20 - 25 °C
3.1: sodium hydroxide / 1 h / 0 - 5 °C
3.2: 2 h / 20 °C
4.1: ammonium chloride; iron / ethanol; water / 6 h / 45 - 50 °C
View Scheme
3-iodo-6-nitro-1H-indazole
70315-70-7

3-iodo-6-nitro-1H-indazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: methanesulfonic acid / dichloromethane; tetrahydrofuran / 5 h / 25 °C
2: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 100 °C
3: ammonium chloride; iron / ethanol; water / 2 h / 50 °C
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 2.5 h / 60 °C
2.1: potassium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 8 h / 60 - 100 °C / Inert atmosphere
2.2: 60 °C
3.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
4.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
View Scheme
Multi-step reaction with 3 steps
1: methanesulfonic acid
2: N-ethyl-N,N-diisopropylamine; palladium diacetate; tris-(o-tolyl)phosphine
3: iron; ammonium chloride
View Scheme
3-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
886230-74-6

3-iodo-6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 100 °C
2: ammonium chloride; iron / ethanol; water / 2 h / 50 °C
View Scheme
Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
2: ammonium chloride; iron / water; ethanol / 2 h / 50 °C
View Scheme
(E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole

(E)-6-nitro-3-[(2-pyridin-2-yl)vinyl]-1H-indazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
2: sodiumsulfide nonahydrate / water; methanol / 60 °C
View Scheme
1-acetyl-3-iodine-6-nitroindazole

1-acetyl-3-iodine-6-nitroindazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate; 1,10-Phenanthroline; copper(l) iodide / N,N-dimethyl-formamide / 8 h / 60 - 100 °C / Inert atmosphere
1.2: 60 °C
2.1: methanesulfonic acid / tetrahydrofuran / 6 h / Reflux
3.1: sodiumsulfide nonahydrate / water; methanol / 60 °C
View Scheme
6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole
150187-67-0

6-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide; iodine / N,N-dimethyl-formamide / 14 h / 10 - 25 °C
1.2: 0.5 h / 20 °C
2.1: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
3.1: ammonium chloride; iron / water; ethanol / 2 h / 50 °C
View Scheme
3,4-dihydro-2H-pyran
110-87-2

3,4-dihydro-2H-pyran

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 2 h / 82 °C
2.1: sodium hydroxide; iodine / N,N-dimethyl-formamide / 14 h / 10 - 25 °C
2.2: 0.5 h / 20 °C
3.1: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; palladium dichloride / N,N-dimethyl-formamide / 12 h / 100 °C / Inert atmosphere
4.1: ammonium chloride; iron / water; ethanol / 2 h / 50 °C
View Scheme
C19H18N4O3

C19H18N4O3

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
With iron; ammonium chloride
2-methyl-5-nitroaniline
99-55-8

2-methyl-5-nitroaniline

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium nitrite; acetic acid
2: iodine; potassium carbonate
3: methanesulfonic acid
4: N-ethyl-N,N-diisopropylamine; palladium diacetate; tris-(o-tolyl)phosphine
5: iron; ammonium chloride
View Scheme
6-nitro-1H-indazole-3-carboxaldehyde
315203-37-3

6-nitro-1H-indazole-3-carboxaldehyde

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: methanesulfonic acid / dichloromethane / 6 h / 20 - 25 °C
2.1: sodium hydroxide / 1 h / 0 - 5 °C
2.2: 2 h / 20 °C
3.1: ammonium chloride; iron / ethanol; water / 6 h / 45 - 50 °C
View Scheme
C13H13N3O4

C13H13N3O4

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / 1 h / 0 - 5 °C
1.2: 2 h / 20 °C
2.1: ammonium chloride; iron / ethanol; water / 6 h / 45 - 50 °C
View Scheme
C12H11BrFN3O

C12H11BrFN3O

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

C31H30FN7O2

C31H30FN7O2

Conditions
ConditionsYield
With sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); johnphos In toluene at 102℃; for 18h;88%
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(Ε)-6-iodo-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Conditions
ConditionsYield
Stage #1: (Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole With sulfuric acid; acetic acid; sodium nitrite In water at -5 - 0℃; for 4h;
Stage #2: With potassium iodide In water at 0℃; for 5.5h;		87%
Stage #1: (Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole With acetic acid; sodium nitrite In water at 0 - 5℃; for 1h;
Stage #2: With iodine; potassium iodide In water at 0 - 5℃; for 3h;		81.2%
Stage #1: (Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole With hydrogenchloride; acetic acid; sodium nitrite In water at 0℃;
Stage #2: With iodine; potassium iodide In dichloromethane; water at 0℃; for 2h;		65%
Stage #1: (Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole With acetic acid; sodium nitrite In water at 0℃; for 2h;
Stage #2: With hydrogenchloride In water at 0℃; for 1.16667h;
Stage #3: With iodine; potassium iodide In water at 0℃; for 2.08333h; Reagent/catalyst;		65.4%
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

Malonic acid monomethyl ester
16695-14-0

Malonic acid monomethyl ester

methyl (E)-3-oxo-3-((3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)amino)propanoate

methyl (E)-3-oxo-3-((3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)amino)propanoate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;86%
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

C19H18N6O*ClH

C19H18N6O*ClH

Conditions
ConditionsYield
Stage #1: (Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole With sodium nitrite In water; acetic acid at 0℃; for 2.5h;
Stage #2: With hydrogenchloride In water; acetic acid at 0℃; for 1.25h;
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

methyl 6-(2-(1-(tetrahydro-2H-pyran-2-yl)-3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzamido)hexanoate
1012060-43-3

methyl 6-(2-(1-(tetrahydro-2H-pyran-2-yl)-3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzamido)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; N,N-dimethyl-formamide / 80 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

methyl 6-(2-(3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzamido)hexanoate
1012060-44-4

methyl 6-(2-(3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzamido)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; N,N-dimethyl-formamide / 80 °C
3.1: toluene-4-sulfonic acid / water; methanol / 1 h / 60 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

N-(5-(hydroxycarbamoyl)pentyl)-2-(3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzamide
1012056-56-2

N-(5-(hydroxycarbamoyl)pentyl)-2-(3-((E)-2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzamide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; N,N-dimethyl-formamide / 80 °C
3.1: toluene-4-sulfonic acid / water; methanol / 1 h / 60 °C
4.1: hydroxylamine / methanol / 0.5 h / 20 °C
4.2: pH 6 - 7
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-methyl 5-(2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)phenoxy)pentanoate
1133966-04-7

(E)-methyl 5-(2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)phenoxy)pentanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; N,N-dimethyl-formamide / 16 h / 80 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-methyl 5-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenoxy)pentanoate
1133966-05-8

(E)-methyl 5-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenoxy)pentanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: caesium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / dichloromethane; N,N-dimethyl-formamide / 16 h / 80 °C
3.1: toluene-4-sulfonic acid / ethanol; water; methanol / 65 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)benzenamine
1133966-14-9

(E)-2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)benzenamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: sodium hydroxide / ISOPROPYLAMIDE / 155 °C / Inert atmosphere
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-methyl 5-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenylamino)pentanoate
1133966-15-0

(E)-methyl 5-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenylamino)pentanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: sodium hydroxide / ISOPROPYLAMIDE / 155 °C / Inert atmosphere
3.1: sodium hydroxide / N,N-dimethyl-formamide / 3 h / 140 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-ethyl 6-oxo-6-(2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)phenylamino)hexanoate
1133966-18-3

(E)-ethyl 6-oxo-6-(2-(3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-ylthio)phenylamino)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: sodium hydroxide / ISOPROPYLAMIDE / 155 °C / Inert atmosphere
3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 123 °C / Inert atmosphere
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-ethyl 6-oxo-6-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenylamino)hexanoate
1133966-19-4

(E)-ethyl 6-oxo-6-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenylamino)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: sodium hydroxide / ISOPROPYLAMIDE / 155 °C / Inert atmosphere
3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 123 °C / Inert atmosphere
4.1: toluene-4-sulfonic acid / water; methanol / 64 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzenamine
1133966-20-7

(E)-2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)benzenamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: sodium hydroxide / ISOPROPYLAMIDE / 155 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / water; methanol / 2 h / Reflux
3.2: pH 10
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-methyl 7-oxo-7-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenylamino)heptanoate
1133966-21-8

(E)-methyl 7-oxo-7-(2-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-ylthio)phenylamino)heptanoate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: hydrogenchloride; sodium nitrite; acetic acid / water / 0 °C
1.2: 2 h / 0 °C
2.1: sodium hydroxide / ISOPROPYLAMIDE / 155 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / water; methanol / 2 h / Reflux
3.2: pH 10
4.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 6 h / 123 °C / Inert atmosphere
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

(E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide

(E)-N-methyl-2-{[3-(2-(pyridin-2-yl)ethenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl]thio}benzamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
1.2: 5.5 h / 0 °C
2.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium nitrite; acetic acid / water / 2 h / 0 °C
1.2: 1.17 h / 0 °C
1.3: 2.08 h / 0 °C
2.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

axitinib
319460-85-0

axitinib

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: acetic acid; sulfuric acid; sodium nitrite / water / 4 h / -5 - 0 °C
1.2: 5.5 h / 0 °C
2.1: potassium carbonate; copper(l) iodide; 2-vinylpyridine / N,N-dimethyl-formamide / 12 h / 100 °C
3.1: water; hydrogenchloride; methanol / 6 h / 60 °C
View Scheme
Multi-step reaction with 3 steps
1.1: sodium nitrite; acetic acid / water / 2 h / 0 °C
1.2: 1.17 h / 0 °C
1.3: 2.08 h / 0 °C
2.1: bis[1,2-bis(diphenylphosphino)ferrocene]-palladium(0); caesium carbonate / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere
3.1: toluene-4-sulfonic acid / water; methanol / 4 h / 65 °C / Inert atmosphere
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

1,1-cyclopropanedicarboxylic acid monomethyl ester
113020-21-6

1,1-cyclopropanedicarboxylic acid monomethyl ester

methyl (E)-1-((3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)carbamoyl)cyclopropane-1-carboxylate

methyl (E)-1-((3-(2-(pyridin-2-yl)vinyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-yl)carbamoyl)cyclopropane-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 2h;
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

(E)-1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-yl)urea

(E)-1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(3-(2-(pyridin-2-yl)vinyl)-1H-indazol-6-yl)urea

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 20 °C
2: trifluoroacetic acid / dichloromethane / 4 h / 20 °C
View Scheme
(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole
886230-76-8

(Ε)-6-amino-3-[2-(pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)indazole

4-chloro-3-(trifluoromethyl)phenyl isocyanate
327-78-6

4-chloro-3-(trifluoromethyl)phenyl isocyanate

C27H23ClF3N5O2

C27H23ClF3N5O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 8h;

(E)-3-[2-(Pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine Specification

The (E)-3-[2-(Pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine has the CAS registry number 886230-76-8. This chemical's molecular formula is C19H20N4O and molecular weight is 320.39. What's more, its systematic name is 3-[(E)-2-(2-pyridyl)vinyl]-1-tetrahydropyran-2-yl-indazol-6-amine. 

Physical properties of (E)-3-[2-(Pyridin-2-yl)ethenyl]-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-6-amine are: (1)ACD/LogP: 2.021; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.98; (4)ACD/LogD (pH 7.4): 2.02; (5)ACD/BCF (pH 5.5): 18.23; (6)ACD/BCF (pH 7.4): 20.19; (7)ACD/KOC (pH 5.5): 269.94; (8)ACD/KOC (pH 7.4): 298.95; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 65.96 Å2; (13)Index of Refraction: 1.676; (14)Molar Refractivity: 93.282 cm3; (15)Molar Volume: 247.852 cm3; (16)Polarizability: 36.98×10-24cm3; (17)Surface Tension: 52.996 dyne/cm; (18)Density: 1.293 g/cm3; (19)Flash Point: 294.188 °C; (20)Enthalpy of Vaporization: 84.602 kJ/mol; (21)Boiling Point: 562.828 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: c1ccnc(c1)/C=C/c2c3ccc(cc3n(n2)C4CCCCO4)N
(2)Std. InChI: InChI=1S/C19H20N4O/c20-14-7-9-16-17(10-8-15-5-1-3-11-21-15)22-23(18(16)13-14)19-6-2-4-12-24-19/h1,3,5,7-11,13,19H,2,4,6,12,20H2/b10-8+
(3)Std. InChIKey: NSPUYMWXWXSVAJ-CSKARUKUSA-N

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