269410-08-4

Usage

Uses

Used in Pharmaceutical Industry:
Pyrazole-4-boronic acid pinacol ester is used as a key intermediate for the preparation of Rho kinase (ROCK) inhibitors and other biologically active compounds. It is crucial in the development of drugs targeting various therapeutic enzymes and kinases, which are essential for treating numerous diseases and conditions.
Used in Chemical Synthesis:
Pyrazole-4-boronic acid pinacol ester is used as a valuable reagent for Suzuki-Miyaura cross-couplings and Ruthenium-catalyzed asymmetric hydrogenation. These reactions are vital in the synthesis of complex organic molecules and contribute to the advancement of chemical research and development.
Used in the Preparation of Inhibitors:
Pyrazole-4-boronic acid pinacol ester is employed as a reagent in the preparation of inhibitors for many highly significant therapeutic enzymes and kinases, including VEGF, Aurora, Rho (ROCK), Janus Kinase 2 (JAK), c-MET, ALK, S-nitrosoglutathione reductase, CDC7, Acetyl-CoA carboxylase, Prosurvival Bcl-2 protein, Viral RNA-Dependent RNA polymerase, Long Chain Fatty Acid Elongase, 6PI3, AKT, Chk1, and Protein Kinase B. These inhibitors play a crucial role in the development of targeted therapies for various diseases, including cancer and other conditions.

InChI:InChI=1/C9H15BN2O2/c1-8(2)9(3,4)14-10(13-8)7-5-11-12-6-7/h5-6H,1-4H3,(H,11,12)

Synthetic route

1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1029716-44-6) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In water at 10 - 25℃; for 4.083h;	94%
With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In tert-butyl methyl ether; 1,2-dichloro-ethane at 0 - 20℃; Large scale;	77.3%
With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In tert-butyl methyl ether; 1,2-dichloro-ethane at 0 - 20℃; Large scale;	77.3%

4-bromo-1H-pyrazole (2075-45-8) + bis(pinacol)diborane (73183-34-3) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane for 12h; Inert atmosphere; Reflux;	94%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In N,N-dimethyl-formamide at 100℃;	25%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Miyaura Borylation Reaction; Inert atmosphere;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 80℃; Miyaura Borylation Reaction; Inert atmosphere;

NH-pyrazole (288-13-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 4h; Inert atmosphere; Glovebox; regioselective reaction;	88%
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 4h; Schlenk technique; Inert atmosphere;	67%

4-chloro-1H-pyrazole (15878-00-9) + bis(pinacol)diborane (73183-34-3) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); XPhos In ethanol at 20℃; for 0.5h;	88%

tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate (552846-17-0) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
at 180℃;	80.2%
at 180℃; for 0.0833333h;	72%

4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester (121669-70-3) + 2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (557087-01-1) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With iPrBu2MgLi In 2-methyltetrahydrofuran at -20 - -10℃; Large scale;	79%

2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (557087-01-1) + 4-bromopyrazole-1-carboxylic acid tert-butyl ester (1150271-23-0) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With n-Bu3MgLi In tetrahydrofuran at -20 - -10℃; Large scale;	76%

NH-pyrazole (288-13-1) + bis(pinacol)diborane (73183-34-3) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin In tetrahydrofuran at 80℃; for 21h; Inert atmosphere; Glovebox;	56%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 1-trimethylsilyl-4-iodopyrazole → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
Stage #1: 4-iodo-1-trimethylsilylpyrazole With isopropylmagnesium chloride In tetrahydrofuran at -6 - 0℃; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	54.8%
Stage #1: 4-iodo-1-trimethylsilylpyrazole With isopropylmagnesium chloride In tetrahydrofuran at -6 - 0℃; for 0.166667h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 2h; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran at -6 - 0℃;	54.8%
Stage #1: 4-iodo-1-trimethylsilylpyrazole With isopropylmagnesium chloride In tetrahydrofuran at -6 - 0℃; for 0.166667h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 2.17h;	54.8%

4-iodopyrazole (3469-69-0) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
Stage #1: With triethylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 80℃; for 18h; Stage #2: 4-iodopyrazole; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In 1,4-dioxane at 80℃; for 18h;

4-iodopyrazole (3469-69-0) + 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1195-66-0) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
Stage #1: 4-iodopyrazole With isopropylmagnesium chloride In tetrahydrofuran at -10℃; for 2.5h; Inert atmosphere; Stage #2: 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 2h; Inert atmosphere;

bis(pinacol)diborane (73183-34-3) → pyrazole-4-boronic acid pinacol ester (269410-08-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / ethanol / 16 h / Inert atmosphere; Reflux 2: 180 °C View Scheme

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 3-[(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-yl)-tert-butoxycarbonyl-amino]benzoic acid ethyl ester (959756-24-2) → 3-{tert-butoxycarbonyl-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-yl]-amino}benzoic acid ethyl ester (959756-25-3)

Conditions	Yield
With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 115℃; for 0.416667h;	100%

glycidyl methyl ether (930-37-0) + pyrazole-4-boronic acid pinacol ester (269410-08-4) → 1-methoxy-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol (1000801-77-3)

Conditions	Yield
at 98℃; for 4h;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 3-(cyanomethylene)azetidine-1-carboxylic acid tert-butyl ester (1153949-11-1) → tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate (1153949-15-5)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃;	100%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In isopropyl alcohol Reflux; Inert atmosphere;	90.5%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In isopropyl alcohol Reflux;	90.5%

2-iodo-propane (75-30-9) + pyrazole-4-boronic acid pinacol ester (269410-08-4) → 1-isopropylpyrazole-4-boronic acid pinacol ester (879487-10-2)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 16h; Inert atmosphere;	100%
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 16h;	61.72%
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃;	57%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropropyltrifluoromethanesulfonate (1182357-90-9) → (3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1309960-93-7)

Conditions	Yield
Stage #1: pyrazole-4-boronic acid pinacol ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 3-{[tert-butyl(dimethyl)silyl]oxy}-2-fluoropropyltrifluoromethanesulfonate In N,N-dimethyl-formamide; mineral oil for 0.333333h; Inert atmosphere;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 2-chloroethyl methyl ether (627-42-9) → 1-(2-methoxyethyl)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (847818-71-7)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Microwave irradiation;	100%
With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Microwave irradiation;	100%
With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; microwave irradiation;	72%
With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 0.5h; Microwave irradiation;	72%

bromoacetopyrrolidine (90892-09-4) + pyrazole-4-boronic acid pinacol ester (269410-08-4) → 1-(pyrrolidin-1-yl)-2-(4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-one (1534350-51-0)

Conditions	Yield
In acetonitrile at 20℃;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 2-(2,2,2-trifluoroethyl)oxirane (407-12-5) → 4,4,4-trifluoro-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)butan-2-ol

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 80℃;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + (2R,5R)-tert-butyl 5-methyl-2-(((methylsulfonyl)oxy)methyl)morpholine-4-carboxylate → tert-butyl (2R,5R)-5-methyl-2-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)morpholine-4-carboxylate

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 24h;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + tert-butyl ((1S,3S,4R)-3-benzyl-4-(3-(hydroxymethyl)phenoxy)cyclopentyl)carbamate → tert-butyl ((1S,3S,4R)-3-benzyl-4-(3-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)phenoxy)cyclopentyl)carbamate

Conditions	Yield
With tributylphosphine; diamide In toluene at 20℃; Mitsunobu Displacement; Sonication;	100%
With tributylphosphine; diamide In toluene at 20℃; Inert atmosphere;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 3-hydroxylmethyl oxetane → 1-(oxetan-3-ylmethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1578484-07-7)

Conditions	Yield
With cyanomethylenetributyl-phosphorane In 1,4-dioxane at 150℃; for 0.75h; Microwave irradiation;	100%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate (552846-17-0)

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 0 - 20℃;	99%
With dmap; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;	99.68%
With dmap In dichloromethane at 20℃; for 4h;	85%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 1-Bromo-2-chloroethane (107-04-0) → 1-(2-chloroethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (877149-79-6)

Conditions	Yield
With caesium carbonate In acetonitrile at 70℃; for 6h;	99%
With caesium carbonate In acetonitrile at 62℃; for 4h;	90%
With caesium carbonate In acetonitrile at 75℃; for 5h;	88%
With caesium carbonate In acetonitrile at 75℃; for 5h;

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 4-(bromomethyl)-1-methyl-1H-pyrazole hydrobromide → 1-methyl-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)methyl)-1H-pyrazole

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 1h;	99%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 2-nitrophenyl bromide (577-19-5) → 4-(2-nitrophenyl)pyrazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide	98.5%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + bromobenzene (108-86-1) → 4-phenyl-1H-pyrazole (10199-68-5)

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate; palladium dichloride In N,N-dimethyl-formamide at 130℃; for 16h; Inert atmosphere;	98%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + tert-butyl (3-bromo-1-((1s,4s)-4-((1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)cyclohexyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)(methyl)carbamate → tert-butyl methyl(1-((1s,4s)-4-((1-methyl-6-oxo-1,6-dihydropyridazin-3-yl)oxy)cyclohexyl)-3-(1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane at 90℃; for 12h; Inert atmosphere; Sealed tube;	98%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + ethyl vinyl ether (109-92-2) → 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1029716-44-6)

Conditions	Yield
Stage #1: pyrazole-4-boronic acid pinacol ester; ethyl vinyl ether With hydrogenchloride In 1,4-dioxane; toluene at 35 - 40℃; Inert atmosphere; Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; toluene for 1h; Product distribution / selectivity;	97.3%
With hydrogenchloride In 1,4-dioxane; toluene at 35℃; Inert atmosphere;	90%
In toluene at 35℃; for 13h; Inert atmosphere;

pyrazole-4-boronic acid pinacol ester (269410-08-4) + Methyl 2-bromobutyrate (3196-15-4, 69043-96-5) → methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)butanoate

Conditions	Yield
With caesium carbonate In Petroleum ether	97%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + (2-chloroethyl)dimethylamine hydrochloride (4584-46-7) → N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine (877149-80-9)

Conditions	Yield
With caesium carbonate In acetonitrile for 5h; Reflux;	95%
With caesium carbonate In acetonitrile at 90℃;	88%
With caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 72.5h;	66%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + ethyl 3-(2-(((trifluoromethyl)sulfonyl)oxy)naphthalene-1-yl)propanoate (1417620-53-1) → ethyl 3-(2-(1H-pyrazol-4-yl)naphthalen-1-yl)propanoate (1426148-40-4)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In 1,4-dioxane for 4h; Suzuki-Miyaura Coupling; Reflux;	95%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 8-bromo-N-tert-butyl-1-(3,5-dichlorophenyl)-7-methoxy-N-methyl-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide → N-tert-butyl-1-(3,5-dichlorophenyl)-7-methoxy-N-methyl-8-(1H-pyrazol-4-yl)-1,4-dihydrochromeno[4,3-c]pyrazole-3-carboxamide

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 90℃; for 1h; Inert atmosphere; Microwave irradiation;	95%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + allyl bromide (106-95-6) → 1-allyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1000801-78-4)

Conditions	Yield
With sodium hexamethyldisilazane In tetrahydrofuran at 70℃;	94%
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 1h; Microwave irradiation;	39%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 2-(bromomethyl)benzonitrile (22115-41-9) → C17H20BN3O2 (930596-18-2)

Conditions	Yield
With potassium carbonate In acetonitrile for 72h; Heating / reflux;	94%

3,4-dihydro-2H-pyran (110-87-2) + pyrazole-4-boronic acid pinacol ester (269410-08-4) → 1-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1003846-21-6)

Conditions	Yield
With trifluoroacetic acid In toluene at 90℃; for 2h;	94%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 4h;	90%
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 4h;	90%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + p-methoxybenzyl chloride (824-94-2) → 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1105039-88-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 5h;	94%
With potassium carbonate In acetonitrile at 80℃; for 5h;	91%
With potassium carbonate In acetonitrile at 60℃; for 15h;	73.3%
With potassium carbonate In acetonitrile at 80℃; for 5h;
With caesium carbonate In acetonitrile for 4h; Reflux;

pyrazole-4-boronic acid pinacol ester (269410-08-4) + 3-chloro-2-methylpropan-2-ol (558-42-9) → 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 160℃; for 2.5h; Microwave irradiation;	94%

pyrazole-4-boronic acid pinacol ester (269410-08-4) + tert-butyl (S)-3-((4-((1R,3R)-3-methyl-2-(2,2,2-trifluoroethyl)-6-(trifluoromethanesulfonyloxy)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)amino)pyrrolidin-1-carboxylate → tert-butyl (S)-3-((4-((1R,3R)-3-methyl-6-(1H-pyrazol-4-yl)-2-(2,2,2-trifluoroethyl)-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)amino)pyrrolidin-1-carboxylate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 16h; Inert atmosphere;	94%

Upstream product

• 3469-69-0 4-iodopyrazole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 288-13-1 NH-pyrazole 
• 73183-34-3 bis(pinacol)diborane 
• 1195-66-0 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 15878-00-9 4-chloro-1H-pyrazole 
• 2075-45-8 4-bromo-1H-pyrazole 
• 121669-70-3 4-iodo-1H-pyrazole-1-carboxylic acid tert-butyl ester 
• 557087-01-1 2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1150271-23-0 4-bromopyrazole-1-carboxylic acid tert-butyl ester 
• 1029716-44-6 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole 
• 552846-17-0 tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazole-1-carboxylate 

Downstream Products

• 1020173-13-0 4-(2-(1H-pyrazol-4-yl)pyridin-4-yloxy)-2-fluorobenzenamine 
• 857531-00-1 AT7867 
• 857530-81-5 2-(4-chloro-phenyl)-2-[4-(1H-pyrazol-4-yl)-phenyl]-ethylamine 
• 761446-44-0 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 877149-80-9 N,N-dimethyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethan-1-amine 
• 917899-03-7 3-(3,4-dichloro-phenyl)-3-[4-(1H-pyrazol-4-yl)-phenyl]-propionic acid 
• 1021733-97-0 tert-butyl 4-(4-{2-[(tert-butoxycarbonyl)amino]-2-[1-(tert-butoxycarbonyl)-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}phenyl)-1H-pyrazole-1-carboxylate 
• 1021733-42-5 4-(2,2-dimethylbutyl)-2-{1-hydroxy-1-methyl-2-[4-(1H-pyrazol-4-yl)phenyl]ethyl}-N,N-dimethyl-1H-imidazole-1-sulfonamide 
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• 877399-35-4 tert-butyl 3-(4-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)-azetidine-1-carboxylate 
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• 1174630-18-2 N-(3-methoxyphenyl)-1-methyl-6-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine 
• 1141878-06-9 4-fluoro-N-{[2-oxo-6-(1H-pyrazol-4-yl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-4-yl]methyl}benzamide 
• 1226795-81-8 C₁₆H₁₂N₄O₂S 

Relevant academic research and scientific papers

Efficient salt-induced kinase inhibitor and preparation method thereof

The invention discloses an efficient salt-induced kinase inhibitor and a preparation method thereof, and the efficient salt-induced kinase inhibitor is characterized by comprising substances of a chemical formula in the invention. The salt-induced kinase inhibitor with excellent performance has high inhibitory activity for in-vitro experiments and also has high cell inhibitory activity.

N-(1H-IMIDAZOL-2-YL)BENZAMIDE COMPOUND AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME AS ACTIVE INGREDIENT

N-(1H-imidazol-2-yl)benzamide compound of formula (I), or a pharmaceutically acceptable salt, a prodrug, a solvate, or a stereoisomer thereof which is a novel compound exhibiting excellent inhibitory activity against IRAK-4, can be used without side effects for efficient prevention and treatment of diseases mediated by IRAK-4 receptors, particularly autoimmune diseases or lymphomas.

PHD INHIBITOR COMPOUNDS, COMPOSITIONS, AND USE

The present invention provides, in part, novel small molecule inhibitors of PHD, having a structure according to Formula (A), and sub-formulas thereof: or a pharmaceutically acceptable salt thereof. The compounds provided herein can be useful for treatment of diseases including heart ( e.g. ischemic heart disease, congestive heart failure, and valvular heart disease), lung (e.g., acute lung injury, pulmonary hypertension, pulmonary fibrosis, and chronic obstructive pulmonary disease), liver (e.g. acute liver failure and liver fibrosis and cirrhosis), and kidney (e.g. acute kidney injury and chronic kidney disease) disease.

Synthesis method of pyrazole-4-pinacolato diboron

The invention discloses a synthesis method of pyrazole-4-pinacolato diboron. According to the method, trimethylbenzene is added as a stable solvent during reaction, so that side reaction in the reaction process is reduced, the method is simple to operate, low in cost and easy to purify and amplify industrial production, and the technical problems that synthesis and purification of pyrazole-4-pinacolato diboron are difficult at present and the like are solved.

Design, synthesis and biological evaluation of pyrazolo[3,4-d]pyrimidine-based protein kinase D inhibitors

The multiple roles of protein kinase D (PKD) in various cancer hallmarks have been repeatedly reported. Therefore, the search for novel PKD inhibitors and their evaluation as antitumor agents has gained considerable attention. In this work, novel pyrazolo[3,4-d]pyrimidine based pan-PKD inhibitors with structural variety at position 1 were synthesized and evaluated for biological activity. Starting from 3-IN-PP1, a known PKD inhibitor with IC50 values in the range of 94–108 nM, compound 17m was identified with an improved biochemical inhibitory activity against PKD (IC50 = 17–35 nM). Subsequent cellular assays demonstrated that 3-IN-PP1 and 17m inhibited PKD-dependent cortactin phosphorylation. Furthermore, 3-IN-PP1 displayed potent anti-proliferative activity against PANC-1 cells. Finally, a screening against different cancer cell lines demonstrated that 3-IN-PP1 is a potent and versatile antitumoral agent.

PROCESSES AND INTERMEDIATES FOR MAKING A JAK INHIBITOR

This invention relates to processes and intermediates for making {1-{1-[3-fluoro-2-(trifluoromethyl)isonicotinoyl]piperidin-4-yl}-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]azetidin-3-yl}acetonitrile, useful in the treatment of diseases related to the activity of Janus kinases (JAK) including inflammatory disorders, autoimmune disorders, cancer, and other diseases.

3-(1H-PYRAZOL-4-YL)PYRIDINE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to pyrazol-4-yl-pyridine compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

3-(1H-PYRAZOL-4-YL)PYRIDINE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR

The present invention is directed to pyrazol-4-yl-pyridine compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.

Compound, pharmaceutical composition with same and application of compound

The invention belongs to the field of pharmaceutical chemicals and relates to a c-Met and HDACs double inhibitor and application thereof. Specifically, the invention relates to a heterocyclic derivative, application of the heterocyclic derivative serving as the c-Met and HDACs double inhibitor or application of the heterocyclic derivative to preparation of an anti-cancer medicine. More specifically, the invention relates to a compound shown in a general formula I, an isomer or medicinal salt thereof. The compound provided by the invention can effectively inhibit the activity of c-Met and HDACsand has potential of being applied to prevention and treatment on diseases such as tumor.

Room-temperature borylation and one-pot two-step borylation/Suzuki-Miyaura cross-coupling reaction of aryl chlorides

A highly efficient room-temperature borylation strategy of aryl chlorides is described. Utilizing Buchwald's second-generation preformed catalyst, boronate esters were obtained for a wide range of substrates in high yield. The method was also applied to Suzuki-Miyaura cross-coupling reaction in a one-pot two-step sequential manner, providing a facile and convenient access to the direct synthesis of biaryl compounds from aryl chlorides.