tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate supplier

Name
tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate
EINECS 800-459-4
CAS No. 877399-74-1
Article Data54
CAS DataBase
Density 1.14 g/cm³
Solubility
Melting Point 114.0 to 118.0 °C
Formula C₁₉H₃₂BN₃O₄
Boiling Point 492.803 °C at 760 mmHg
Molecular Weight 377.292
Flash Point 251.838 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-[1-(tert-Butoxycarbonyl)piperidin-4-yl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;4-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl)piperidine-1-carboxylicacid tert-butyl ester;4-[4-(4,4,5,5-Tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylicacid tert-butyl ester;tert-Butyl4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate;tert-Butyl4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate;
PSA 65.82000
LogP 2.69220

Synthetic route

: 877399-50-3
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

: 73183-34-3
bis(pinacol)diborane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With C54H44NO2PPdS; potassium acetate In tetrahydrofuran at 80℃; for 24h; Miyaura Borylation Reaction; Inert atmosphere; Sealed tube;	94%
With isopropylmagnesium chloride In tetrahydrofuran at -10 - 30℃; for 9h; Inert atmosphere; Large scale;	81%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 0.166667h; Inert atmosphere;	44%

: 877399-73-0
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 73183-34-3
bis(pinacol)diborane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;	87.9%
With bis-triphenylphosphine-palladium(II) chloride; potassium acetate In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;	87.9%
With potassium acetate; tetrakis(triphenylphosphine) palladium(0) In dimethyl sulfoxide at 80℃; for 2h; Inert atmosphere;	83%

: 877399-73-0
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1195-66-0
2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -10 - 0℃; for 5.25h; Large scale reaction; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 25℃; for 10.75h; Large scale reaction;	81%
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -10 - 20℃; for 2h; Inert atmosphere; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	61.5%
With isopropylmagnesium chloride In tetrahydrofuran at 0 - 30℃;
In tetrahydrofuran

: 877399-50-3
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

: 1195-66-0
2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20 - 30℃; for 12h; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 30℃; for 6h;	80%

: 877399-50-3
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

: 185990-03-8
dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 1h;	61%

: 877399-50-3
4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

: 61676-62-8
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 4-(4-bromo-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 20 - 30℃; for 12h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20 - 30℃; for 6h;	60%
With n-butyllithium In tetrahydrofuran; hexane at -70 - 20℃; for 3h;	51%

: 269410-08-4
pyrazole-4-boronic acid pinacol ester

: 141699-59-4
1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20 - 100℃; for 18h;	48%
With caesium carbonate In N,N-dimethyl-formamide at 90℃; Inert atmosphere;	44%
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h;	39%

: 141699-59-4
1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: pyrazole-4-boronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate In N,N-dimethyl-formamide at 100℃;	29%
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 110 °C / Inert atmosphere; Microwave irradiation 2: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere 1.2: 12 h / 100 °C / Inert atmosphere 2.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere View Scheme

: 269410-08-4
pyrazole-4-boronic acid pinacol ester

: 180695-79-8
tert-butyl 4-bromo-1-piperidinecarboxylate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With caesium carbonate In N,N-dimethyl acetamide at 85℃; for 12h; Inert atmosphere;	5%

: 109384-19-2
t-butyl 4-hydroxy piperidine-1-carboxylate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 110 °C / Inert atmosphere; Microwave irradiation 3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate / dimethyl sulfoxide / 3 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: dmap; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 4 °C / Inert atmosphere 2.2: 12 h / 100 °C / Inert atmosphere 3.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / dimethyl sulfoxide / 2 h / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1.1: triethylamine / tert-butyl methyl ether / 1 h / -5 - 22 °C / Inert atmosphere 2.1: caesium carbonate / n-methyl-2-pyrrilidone / 18.5 h / 80 °C 3.1: isopropylmagnesium chloride / tetrahydrofuran / 5.25 h / -10 - 0 °C / Large scale reaction 3.2: 10.75 h / 20 - 25 °C / Large scale reaction View Scheme

: 5382-16-1
4-HYDROXYPIPERIDINE

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: sodium hydride / N,N-dimethyl-formamide / 12 h / 80 °C 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: triethylamine 2: triethylamine; dmap / dichloromethane 3: sodium hydride / N,N-dimethyl-formamide 4: tetrahydrofuran View Scheme
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 80 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere; Sealed tube View Scheme

: 24424-99-5
di-tert-butyl dicarbonate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: sodium hydride / N,N-dimethyl-formamide / 12 h / 80 °C 4: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 12 h / 110 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 80 °C 4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 12 h / 100 °C / Inert atmosphere; Sealed tube View Scheme

: 73183-34-3
bis(pinacol)diborane

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 21 h / 80 °C / Inert atmosphere; Glovebox 2: caesium carbonate / N,N-dimethyl-formamide / 120 °C / Inert atmosphere View Scheme

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 13675-18-8
tetrahydroxydiboron

: 36437-19-1
2-chloromalonaldehyde

: 1196486-69-7
tert-butyl 4-hydrazino-piperidine-1-carboxylate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-chloromalonaldehyde; tert-butyl 4-hydrazino-piperidine-1-carboxylate With boron trifluoride diethyl etherate In toluene Reflux; Inert atmosphere; Stage #2: tetrahydroxydiboron With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4h; Inert atmosphere; Stage #3: 2,3-dimethyl-2,3-butane diol Inert atmosphere;	10.1 g

Yield

Stage #1: 2-chloromalonaldehyde; tert-butyl 4-hydrazino-piperidine-1-carboxylate With boron trifluoride diethyl etherate In toluene Reflux; Inert atmosphere;
Stage #2: tetrahydroxydiboron With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 80℃; for 4h; Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diol Inert atmosphere;

10.1 g

...Expand

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 13675-18-8
tetrahydroxydiboron

: 2065-75-0
2-Bromo-malonaldehyde

: 1196486-69-7
tert-butyl 4-hydrazino-piperidine-1-carboxylate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 2-Bromo-malonaldehyde; tert-butyl 4-hydrazino-piperidine-1-carboxylate With boron trifluoride diethyl etherate In toluene Reflux; Inert atmosphere; Stage #2: tetrahydroxydiboron With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 20℃; for 12h; Inert atmosphere; Stage #3: 2,3-dimethyl-2,3-butane diol Inert atmosphere;	8.8 g

Yield

Stage #1: 2-Bromo-malonaldehyde; tert-butyl 4-hydrazino-piperidine-1-carboxylate With boron trifluoride diethyl etherate In toluene Reflux; Inert atmosphere;
Stage #2: tetrahydroxydiboron With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-ethyl-N,N-diisopropylamine; triphenylphosphine In ethanol at 20℃; for 12h; Inert atmosphere;
Stage #3: 2,3-dimethyl-2,3-butane diol Inert atmosphere;

8.8 g

...Expand

: 79099-07-3
N-tert-butyloxycarbonylpiperidin-4-one

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrazine hydrate / ethanol / 0.5 h / 20 °C 1.2: 2 h / 20 °C 2.1: boron trifluoride diethyl etherate / toluene / Reflux; Inert atmosphere 2.2: 12 h / 20 °C / Inert atmosphere 2.3: Inert atmosphere View Scheme

: 24608-52-4
tert-butyl chloroformate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine 2: triethylamine; dmap / dichloromethane 3: sodium hydride / N,N-dimethyl-formamide 4: tetrahydrofuran View Scheme

: 76-09-5
2,3-dimethyl-2,3-butane diol

: 877399-73-0
tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: tert-butyl 4-(4-iodo-1H-pyrazol-1-yl)piperidine-1-carboxylate With isopropylmagnesium chloride In tetrahydrofuran at -25 - 20℃; for 2h; Inert atmosphere; Stage #2: With Trimethyl borate In tetrahydrofuran at 5 - 10℃; for 2.5h; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran at 60℃; for 2.5h; Temperature; Concentration;

: 269410-08-4
pyrazole-4-boronic acid pinacol ester

N-Boc-piperidine-4-yl halide: N-Boc-piperidine-4-yl halide

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1175273-62-7
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 35℃; for 3h;	100%
Stage #1: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate With trifluoroacetic acid at 0 - 20℃; for 0.166667h; Stage #2: With hydrogenchloride In 1,4-dioxane	100%
With hydrogenchloride In 1,4-dioxane at 35℃; for 3h;
With hydrogenchloride In ethyl acetate at 20℃; for 2h;

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; ethyl acetate at 20℃;	100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 1h;	100%
With hydrogenchloride In 1,4-dioxane at 20℃; for 16h;
With hydrogenchloride In 1,4-dioxane at 35℃; for 3h;

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: (S)-methyl 6-bromo-2-methyl-5-propoxy-3,4-dihydroquinoline-1(2H)-carboxylate

: (S)-methyl 6-(1-(1-(tert-butoxycarbonyl)piperidin-4-yl)-1H-pyrazol-4-yl)-2-methyl-5-propoxy-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions

Conditions	Yield
With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); caesium carbonate In 1,4-dioxane; water at 100℃; for 5h; Microwave irradiation;	100%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1175708-03-8
4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazol-1-yl)piperidine

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 4h;	100%
With trifluoroacetic acid In dichloromethane at 20 - 40℃; for 0.25h;	100%
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 6-bromo-3-chloro-4-methoxypyrazolo[1,5-a]pyridine

: tert-butyl 4-(4-(3-chloro-4-methoxypyrazolo[1,5-a]pyridin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere; Sealed tube;	100%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1346245-13-3
3-chloro-N-(3,5-dimethoxyphenyl)quinoxalin-6-amine

: tert-butyl 4-(4-(7-((3,5-dimethoxyphenyl)amino)quinoxalin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;	99%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: (S)-2-((4-(5-bromopyrimidine-2-yl)morpholin-2-yl)methyl)-6-(3-fluorophenyl)pyridazine-3(2H)-one

: (S)-tert-butyl 4-(4-(2-(2-((3-(3-fluorophenyl)-6-oxopyridazin-1(6H)-yl)methyl)morpholino)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere;	98%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;	86 mg

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 6-bromo-4-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

: tert-butyl 4-(4-(3-cyano-4-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 80℃; Inert atmosphere; Sealed tube;	98%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1450642-85-9
5-bromo-3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

: 1562305-29-6
tert-butyl 4-(4-(3-(1-(3,5-difluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water at 20℃; for 15h;	96%

: 59489-71-3
5-amino-2-bromopyrazine

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: tert-butyl 4-(4-(5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 90℃; for 16h; Suzuki Coupling; Inert atmosphere; Sealed tube;	96%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 911434-05-4
5-bromo-2-methyl-3-nitropyridine

: 1229457-95-7
tert-butyl 4-[4-(6-methyl-5-nitropyridin-3-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Conditions

Conditions	Yield
Stage #1: 5-bromo-2-methyl-3-nitropyridine; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.333333h; Stage #2: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate With potassium carbonate In 1,2-dimethoxyethane; isopropyl alcohol at 20 - 85℃;	95%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1569895-70-0
(R)-5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine

: 1569895-72-2
C31H38Cl2FN5O5

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere;	95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 3h; Suzuki Coupling;	85%

: 5-bromo-3-[1 (R)-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-2-ylamine

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 4-(4-{6-amino-5-[(R)-1-(2,6-dichloro-3-fluoro-phenyl)-ethoxy]-pyridin-3-yl}-pyrazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,2-dimethoxyethane; water at 90℃; for 3h; Suzuki coupling; Inert atmosphere;	94%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide for 16h; Inert atmosphere;	80%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; caesium carbonate In water; benzene at 70℃; for 5h; Inert atmosphere;	76%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 7-bromo-6-methylimidazo[1,2-a]pyridine

: tert-butyl 4-(4-(6-methylimidazo[1,2-a]pyridin-7-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 50℃; for 1.5h;	93%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-tert-butyloxycarbonylaminopyridine

: tert-butyl 4-(4-(6-((tert-butoxycarbonyl)amino)-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere;	92.3%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 183208-35-7
5-bromo-1H-pyrrolo[2,3-b]pyridine

: 1562305-10-5
4-(4-(1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 2h; Suzuki-Miyaura Coupling;	92%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux;	71%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,2-dimethoxyethane; water Inert atmosphere; Reflux;	71%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 20℃; for 15h;	46.2%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere;

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 5-bromo-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)-2-benzyloxycarbonylaminopyridine

: tert-butyl 4-(4-(6-(((benzyloxy)carbonyl)amino)-5-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridin-3-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere;	91.8%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1239369-33-5
C13H10BrN3O

: 1239369-35-7
C26H30N6O3

Conditions

Conditions	Yield
Stage #1: tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate; C13H10BrN3O With bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane at 20℃; for 0.5h; Suzuki coupling; Stage #2: With sodium carbonate In 1,4-dioxane; water for 3h; Suzuki coupling; Reflux;	91%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: methyl 6-((6-bromo-2-oxobenzo[d]thiazole-3(2H)-yl)methyl)nicotinate

: methyl 6-((6-(1-(1-(tert-butoxycarbonyl)piperidine-4-yl)-1H-pyrazole-4-yl)-2-oxobenzo[d]thiazole-3(2H)-yl)methyl)nicotinate

Conditions

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); caesium carbonate In 1,4-dioxane; water at 100℃; for 18h;	90.7%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1-((1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methyl)-6-(1-methyl-1H-pyrazol-4-yl)-1H-[1 , 2,3]triazolo[4,5-b]pyrazine

: tert-butyl 4-(4-(2-(3-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)piperidin-1-yl)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 2h; Inert atmosphere;	90%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 12h;	90%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: N-(3-(2-(3-amino-6-bromopyrazin-2-yl)-1H-benzo[d]imidazol-1-yl)phenyl)acetamide

: tert-butyl 4-(4-(6-(1-(3-acetamidophenyl)-1H-benzo[d]imidazol-2-yl)-5-aminopyrazin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;	90%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 691872-15-8
3-hydroxy-5-bromo-2-nitropyridine

: C18H23N5O5

Conditions

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 16h; Inert atmosphere; Large scale;	90%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 877399-47-8
(R)-5-bromo-N,N-bis-(tert-butoxycarbonyl)-3-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)pyridine-2-amine

: C36H46Cl2FN5O7

Conditions

Conditions	Yield
With 5%-palladium/activated carbon; potassium carbonate In water; toluene at 70℃; for 4h; Temperature; Reagent/catalyst; Suzuki Coupling; Inert atmosphere;	90%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: (S)-4-(2-chloro-6-(3,5-dimethylisoxazol-4-yl)quinazolin-4-yl)-3-phenylmorpholine

: tert-butyl (S)-4-(4-(6-(3,5-dimethylisoxazol-4-yl)-4-(3-phenylmorpholino)quinazolin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 90℃; for 1.5h; Inert atmosphere;	87%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: (5-bromo-3-(2-methoxybenzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate

: tert-butyl 4-(4-(3-(2-methoxybenzoyl)-1-(pivaloyloxymethyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 1.5h; Suzuki-Miyaura Coupling;	86%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: (R)-2-bromo-7-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)quinoxaline

: tert-butyl (R)-4-(4-(7-(1-(2,6-dichloro-3-fluorophenyl)ethoxy)quinoxalin-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetrabutylammomium bromide; caesium carbonate In water; toluene at 80℃; for 5h; Inert atmosphere;	86%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: (5-bromo-3-(2-chloro-4-(phenoxymethyl)benzoyl)-1H-pyrrolo[2,3-b]pyridin-1-yl)methyl pivalate

: tert-butyl 4-(4-(3-(2-chloro-4-(phenoxymethyl)benzoyl)-1-((pivaloyloxy)methyl)-1H-pyrrolo[2,3-b]pyridin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃; for 1.5h; Suzuki-Miyaura Coupling;	85%

: 877399-74-1
tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

: 1-[(2S)-6-bromo-5-(2-fluorophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-1-yl]ethan-1-one

: (S)-tert-butyl 4-(4-(1-acetyl-5-(2-fluorophenoxy)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

Conditions

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 80℃; for 12h;	85%

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate Specification

The tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate is an organic compound with the formula C₁₉H₃₂BN₃O₄. The systematic name of this chemical is tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]piperidine-1-carboxylate. With the CAS registry number 877399-74-1, it is also named as 1-piperidinecarboxylic acid, 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]-, 1,1-dimethylethyl ester.

Physical properties about tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate are: (1)#H bond acceptors: 7; (2)#Freely Rotating Bonds: 4; (3)Polar Surface Area: 65.82 Å²; (4)Index of Refraction: 1.539; (5)Molar Refractivity: 103.586 cm³; (6)Molar Volume: 330.852 cm³; (7)Polarizability: 41.065×10^-24cm³; (8)Surface Tension: 37.581 dyne/cm; (9)Density: 1.14 g/cm³; (10)Flash Point: 251.838 °C; (11)Enthalpy of Vaporization: 75.981 kJ/mol; (12)Boiling Point: 492.803 °C at 760 mmHg.

You can still convert the following datas into molecular structure:
(1)SMILES: B1(OC(C(O1)(C)C)(C)C)c2cnn(c2)C3CCN(CC3)C(=O)OC(C)(C)C
(2)InChI: InChI=1/C19H32BN3O4/c1-17(2,3)25-16(24)22-10-8-15(9-11-22)23-13-14(12-21-23)20-26-18(4,5)19(6,7)27-20/h12-13,15H,8-11H2,1-7H3
(3)InChIKey: QSQWENQPOSRWLP-UHFFFAOYAI
(4)Std. InChI: InChI=1S/C19H32BN3O4/c1-17(2,3)25-16(24)22-10-8-15(9-11-22)23-13-14(12-21-23)20-26-18(4,5)19(6,7)27-20/h12-13,15H,8-11H2,1-7H3
(5)Std. InChIKey: QSQWENQPOSRWLP-UHFFFAOYSA-N

Product Name

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Synthetic route

tert-Butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate Specification

Related Products

Hot Products