761446-44-0

Basic information

• Product Name: 1-Methyl-4-pyrazole boronic acid pinacol ester
• Synonyms: 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-;1-METHYL- 4-PYRAZOLEBORONIC ACID PINACOL ESTER;1-METHYL-4-(4,4,5,5-TERAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRAZOLE;1-methyl-4-(4，4，5，5-tetramethyl-1，3，2-dioxaborolan-2-yl)-1H-;1-Methyl-4-pyrazoleboronic acid pinacol ester, 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-4-(4,4,5-trimethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole;1-Methyl-1H-pyrazole-4-boronic acid pinacol;1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole1-Methylpyrazole-4-boronic acid pinacol ester
• CAS NO: 761446-44-0
• Molecular Formula: C₁₀H₁₇BN₂O₂
• Molecular Weight: 208.07
• EINECS: 1312995-182-4
• Product Categories: Organoborons;Pyrazole;Boronic acid;Heterocyclic Building Blocks;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronate Esters;Organometallic Reagents
• Mol File: 761446-44-0.mol
• Article Data: 22

Chemical Properties

• Melting Point: 59-64 °C(lit.)
• Boiling Point: 308.3 °C at 760 mmHg
• Flash Point: 140.3 °C
• Appearance: Off-white to yellow/Crystals
• Density: 1.05 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.505
• Storage Temp.: Refrigerator (+4°C)
• Solubility: Chloroform (slightly), Methanol (Slightly)
• PKA: 2.09±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 1-Methyl-4-pyrazole boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-4-pyrazole boronic acid pinacol ester(761446-44-0)
• EPA Substance Registry System: 1-Methyl-4-pyrazole boronic acid pinacol ester(761446-44-0)

Safety Data

• Hazard Codes: Xn,F,Xi
• Statements: 22-36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: No
• HazardClass: IRRITANT
• Hazardous Substances Data: 761446-44-0(Hazardous Substances Data)

Usage

Chemical Properties

White to light yellow crystal powde

Uses

Different sources of media describe the Uses of 761446-44-0 differently. You can refer to the following data:
1. 1-Methyl-4-pyrazole boronic acid pinacol ester is a reagent used for:Suzuki-Miyaura cross-coupling reactions1,2,3? ;Transesterification reactions4Reagent used for preparation of? ;Aminothiazoles as γ-secretase modulators5? ;Amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy6? ;Pyridine derivatives as TGF-β1 and activin A signalling inhibitors7? ;MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer8.
2. suzuki reaction
3. It is a reagent used for Suzuki-Miyaura cross-coupling reactions, transesterification reactions. It is involved in several reactions as a reagent for the preparation of aminothiazoles as γ-secretase modulators,amino-pyrido-indol-carboxamides, as potential JAK2 inhibitors for myeloproliferative disorders therapy, pyridine derivatives as TGF-β1 and active A signaling inhibitors and MK-2461 analogs as inhibitors of c-Met kinase for the treatment of cancer.

InChI:InChI=1/C10H17BN2O2/c1-9(2)10(3,4)15-11(14-9)8-6-12-13(5)7-8/h6-7H,1-5H3

Synthetic route

pyrazole-4-boronic acid pinacol ester (269410-08-4) + methyl iodide (74-88-4) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃; for 4h;	93%
With sodium hydride In tetrahydrofuran at 20℃;	90%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 3h;	72%
With sodium hydride In tetrahydrofuran; mineral oil at 0 - 60℃; for 8h; Inert atmosphere;	63%

2,3-dimethyl-2,3-butane diol (76-09-5) + (1-methyl-1H-pyrazol-4-yl)boronic acid (847818-55-7) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
With 4 A molecular sieve In tetrahydrofuran at 20℃; for 2h;	80%
With alkaline lipase In tetrahydrofuran; ethanol at -15 - -10℃; for 12h; Concentration; Reagent/catalyst; Molecular sieve; Large scale; Enzymatic reaction;	92.5 kg

1-methyl-1H-pyrazole (930-36-9) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium Stage #2: With Trimethyl borate In tetrahydrofuran at -90℃; Stage #3: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran	80%

4-bromo-1-methyl-1H-pyrazole (15803-02-8) + bis(pinacol)diborane (73183-34-3) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 5h; Inert atmosphere;	27.1%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 100℃; for 12h; Suzuki-Miyaura Coupling;

pyrazole-4-boronic acid pinacol ester (269410-08-4) + methyl bromide (74-83-9) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
With caesium carbonate In acetonitrile Inert atmosphere;

2,3-dimethyl-2,3-butane diol (76-09-5) + methyldiazene (22038-72-8, 26981-93-1, 51943-20-5) + C19H43BN2O4 → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
With toluene-4-sulfonic acid In toluene Reflux;

4-chloro-1-methyl-1H-pyrazole (35852-81-4) + bis(pinacol)diborane (73183-34-3) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

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 2h;

4-iodo-1-methyl-1H-pyrazole (39806-90-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
Stage #1: 4-iodo-1-methyl-1H-pyrazole With isopropylmagnesium chloride; lithium chloride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 0 - 20℃; for 1.5h;	1 g

1-methyl-1H-pyrazole (930-36-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (847818-74-0) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions

Yield

Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer In hexane at 20℃; Glovebox; Inert atmosphere; Stage #2: With 4,4'-di-tert-butyl-2,2'-bipyridine In hexane at 20℃; Glovebox; Inert atmosphere; Stage #3: 1-methyl-1H-pyrazole In hexane at 20℃; for 5h; Reagent/catalyst; Solvent; Glovebox; Inert atmosphere; Overall yield = 67 percent; regioselective reaction;

pyrazole-4-boronic acid pinacol ester (269410-08-4) + methyl halide → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
With potassium carbonate In acetonitrile

4-bromo-1-methyl-1H-pyrazole (15803-02-8) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0)

Conditions	Yield
Stage #1: 4-bromo-1-methyl-1H-pyrazole With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -75 - -65℃; Inert atmosphere; Large scale; Stage #2: 2,3-dimethyl-2,3-butane diol In tetrahydrofuran; hexane; toluene at -75 - 20℃; Large scale;

3-bromo-5-trifluoromethylbenzoic acid methyl ester + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → methyl 3-(1-methyl-1H-pyrazol-4-yl)-5-(trifluoromethyl)benzoate (1237536-10-5)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 3h; Suzuki Coupling;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 3h;	100%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 3h;	100%

7-chloro-1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-5H-pyrido[4, 3-b ]indole-4-carboxamide (1160756-09-1) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 1-{[(1R)-1-cyclopropyl-2,2,2-trifluoroethyl]amino}-7-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4,3-b]indole-4-carboxamide (1160756-20-6)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	100%

N-(3-(5-bromo-1H-benzo[d]imidazol-1-yl)-5-(1-(phenylsulfonyl)-1H-indol-3-yl)phenyl)acetamide (1430728-70-3) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → N-(3-(5-(1-methyl-1H-pyrazol-4-yl)-1H-benzo[d]imidazol-1-yl)-5-(1-(phenylsulfonyl)-1H-indol-3-yl)phenyl)acetamide (1430728-71-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 90℃; for 2h; Inert atmosphere;	100%

3-[1-(4-bromo-2-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-16-6) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-88-2)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Microwave irradiation;	100%

3-[1-(4-bromo-3-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-34-8) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[3-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-91-7)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 120℃; for 1h; Microwave irradiation;	100%

(8R)-3-[1-(4-bromo-2-fluorophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-89-3) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → (8R)-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-{1-[2-fluoro-4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-90-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water Reflux;	100%

(8R)-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-[1-(4-chlorophenyl)cyclopropyl]-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-04-2) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → (8R)-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-3-{1-[4-(1-methyl-1H-pyrazol-4-yl)phenyl]cyclopropyl}-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine (1403396-43-9)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tricyclohexylphosphine In 1,4-dioxane; water at 140℃; for 2h; Microwave irradiation;	100%

5-bromo-3-chloroisoquinoline (1029720-67-9) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 3-chloro-5-(1-methyl-1H-pyrazol-4-yl)isoquinoline (1578245-81-4)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 105℃; for 1.5h; Suzuki Coupling; Microwave irradiation;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane at 110℃; for 2h; Microwave irradiation;

8-chloro-2-(methylsulfanyl)pyrido[3,4-d]pyrimidine (1578245-95-0) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 8-(1-methyl-1H-pyrazol-4-yl)-2-(methylthio)pyrido[3,4-d]pyrimidine (1578245-98-3)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran; water at 65℃; for 18h;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In tetrahydrofuran at 65℃; for 18h; Suzuki Coupling;	100%

3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 24h; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 24h; Suzuki Coupling; Inert atmosphere;

tert-butyl (R)-3-(7-bromo-2,2-dioxido-1,4-dihydro-3H-benzo[c][1,2,6]thiadiazin-3-yl)pyrrolidine-1-carboxylate + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → tert-butyl (R)-3-(7-(1-methyl-1H-pyrazol-4-yl)-2,2-dioxido-1,4-dihydro-3H-benzo[c][1,2,6]thiadiazin-3-yl)pyrrolidine-1-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In 1,4-dioxane; water at 90℃; for 1h; Sealed tube;	100%

ethyl 9'-(1-(tertbutoxycarbonyl)-1H-pyrazol-4-yl)-10'-methoxy-2'-oxo-2',7'-dihydrospiro[cyclobutane-1,6'pyrido[2,1-a]isoquinoline]-3'-carboxylate + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → ethyl 10'-methoxy-9'-(1-methyl-1H-pyrazol-4-yl)-2'-oxo-2',7'-dihydrospiro[cyclobutane-1,6'-pyrido[2,1-a]isoquinoline]-3'-carboxylate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%

(S)-4-(4-(5-(1-amino-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazin-1-yl)-6-bromopyrrolo[1,2-b]pyridazine-3-carbonitrile + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → (S)-4-(4-(5-(1-amino-1-(4-fluorophenyl)ethyl)pyrimidin-2-yl)piperazin-1-yl)-6-(1-methyl-1H-pyrazol-4-yl)pyrrolo[1,2-b]pyridazine-3-carbonitrile

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%

4-amino-3-iodobenzoic acid methyl ester (19718-49-1) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → methyl 4-amino-3-(1-methyl-1H-pyrazol-4-yl)benzoate

Conditions	Yield
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride In 1,4-dioxane; water at 90℃; for 8h; Inert atmosphere;	100%

2-amino-6-bromo-4-methoxypyrazolo[1,5-a]pyridine-3-carbonitrile + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 2-amino-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;	100%

4-bromo-2-methylpyridine (22282-99-1) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 2-methyl-4-(1-methyl-1H-pyrazol-4-yl)pyridine

Conditions	Yield
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 85℃; for 12h; Suzuki Coupling; Inert atmosphere;	100%

4-Bromo-2-nitroaniline (875-51-4) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 4-(1-methyl-1H-pyrazol-4-yl)-2-nitroaniline (959909-79-6)

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In ISOPROPYLAMIDE; water at 80℃; for 1h; Suzuki Coupling;	99%
With sodium carbonate In N,N-dimethyl acetamide; water at 80℃; for 1h; Inert atmosphere;	99%
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In N,N-dimethyl acetamide; water at 80℃; for 1h; Suzuki Coupling;	99%

8-amino-3-bromoimidazo<1,2-a>pyrazine (117718-92-0) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → C10H10N6

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 80℃; for 16h;	99%
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; water at 80℃; for 16h;	99%

9-benzenesulfonyl-3-bromo-5-hydroxy-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile (1200130-75-1) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 9-benzenesulfonyl-5-hydroxy-3-(1-methyl-1H-pyrazol-4-yl)-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile (1200130-78-4)

Conditions	Yield
With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; acetonitrile at 140℃; for 0.5h; Microwave irradiation;	99%

C25H34ClN3O3Si (1346245-14-4) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → C29H39N5O3Si (1346245-11-1)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); XPhos In 1,4-dioxane; water at 80℃; Inert atmosphere;	99%

6-bromo-2-(trimethylsilyl)furo[3,2-b]pyridine + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → C14H17N3OSi

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine In 1,2-dimethoxyethane; water for 1.16667h; Inert atmosphere; Reflux;	99%

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 1-methyl-1H-pyrazol-4-ol (78242-20-3)

Conditions	Yield
With water; dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 20℃; for 3h;	99%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 25℃; for 3h; Inert atmosphere;	98%
With dihydrogen peroxide; sodium hydroxide In tetrahydrofuran at 0 - 5℃; for 0.883333h;	38.2%

2-bromo-4-nitrotoluene (7745-93-9) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 1-methyl-4-(2-methyl-5-nitrophenyl)-1H-pyrazole

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 90℃; for 10h; Inert atmosphere;	99%

tert-butyl 4-(4-bromo-2-cyanophenoxy)piperidine-1-carboxylate (1292317-56-6) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → C21H26N4O3

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In water; N,N-dimethyl-formamide at 80℃; for 16h; Suzuki Coupling; Inert atmosphere;	99%

tert-butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate (1123169-45-8) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → tert-butyl 6-(1-methyl-1H-pyrazol-4-yl)-3,4-dihydroquinoline-1(2H)-carboxylate

Conditions	Yield
Stage #1: tert-butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate; 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole With caesium carbonate In 1,4-dioxane; water for 0.333333h; Suzuki Coupling; Inert atmosphere; Stage #2: With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate In 1,4-dioxane; water at 100℃; for 2.16667h; Suzuki Coupling; Inert atmosphere;	99%
With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	99%
With (2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1 ‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; caesium carbonate In 1,4-dioxane; water at 100℃; for 2h; Inert atmosphere;	99%

6-bromo-4-methoxy-2-methylpyrazolo[1,5-a]pyridine-3-carbonitrile + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 4-methoxy-2-methyl-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine-3-carbonitrile

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere;	99%

4-bromo-2-fluorobenzyl alcohol (188582-62-9) + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 4-(4-hydroxymethyl-3-fluorophenyl)-1-methyl-1H-pyrazole (1418201-67-8)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h;	98%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In tetrahydrofuran; water at 160℃; for 0.166667h; Sealed tube; Microwave irradiation;
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran; water at 160℃; for 0.166667h; Microwave irradiation; Sealed tube;

5-(5-((2-chloropyridin-4-yl)oxy)-6-methylpyridin-2-yl)-4-methoxy-2-(methylthio)pyrimidine + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 4-methoxy-5-(6-methyl-5-((2-( 1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-2-(methylthio)pyrimidine

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

5-bromo-1-methyl-N-[2-(trifluoromethyl)pyridin-4-yl]-1H-indole-3-carboxamide + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → 1-methyl-5-(1-methyl-1H-pyrazol-4-yl)-N-[2-(trifluoromethyl)pyridin-4-yl]-1H-indole-3-carboxamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 100℃; for 1.5h;	98%

methyl 4-bromo-1-(4-bromo-5-(isopropylthio)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate + 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (761446-44-0) → methyl 4-bromo-1-(5-(isopropylthio)-4-(1-methyl-1H-pyrazol-4-yl)thiazol-2-yl)-3-methyl-1H-pyrazole-5-carboxylate

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In tetrahydrofuran at 90℃; for 16h; Inert atmosphere; Sealed tube;	98%
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); potassium carbonate In tetrahydrofuran at 20 - 90℃; for 16h; Inert atmosphere; Sealed tube;	94%

Upstream product

• 269410-08-4 pyrazole-4-boronic acid pinacol ester 
• 74-83-9 methyl bromide 
• 73183-34-3 bis(pinacol)diborane 
• 39806-90-1 4-iodo-1-methyl-1H-pyrazole 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 35852-81-4 4-chloro-1-methyl-1H-pyrazole 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 22038-72-8 methyldiazene 
• 930-36-9 1-methyl-1H-pyrazole 
• 74-88-4 methyl iodide 
• 847818-55-7 (1-methyl-1H-pyrazol-4-yl)boronic acid 
• 15803-02-8 4-bromo-1-methyl-1H-pyrazole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 

Downstream Products

• 936011-06-2 7-[(2,4-dimethoxybenzyl)amino]-3-(1-methyl-1H-pyrazol-4-yl)-5H-pyrido[4',3':4,5]cyclohepta[1,2-b]pyridin-5-one 
• 879487-28-2 C₂₅H₃₀FN₅OSi 
• 1186126-66-8 1-methyl-4-(2-phenylcyclohex-1-enyl)-1H-pyrazole 
• 1186126-68-0 ethyl 3-(1-methyl-1H-pyrazol-4-yl)benzoate 
• 1180009-56-6 1-acetyl-1'-methyl-5-phenyl-4,5-dihydro-1H,1'H-3,4'-bipyrazole 
• 1185763-71-6 3-(4-methoxy-benzyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine 
• 1034044-86-4 6-[(4-tert-Butylphenyl)sulfonyl]-7-methyl-8-(1-methyl-1H-pyrazol-4-yl)-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepine 
• 1201790-53-5 N-{4-[3-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-9H-pyrrolo[2,3-b:5,4-c']dipyrid-4-yl]phenyl}methanesulfonamide 
• 1160064-36-7 (2S,3S,5R)-2-benzyl-3-{(3-chloro-5-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-5-ethyl-pyrrolidine-1-carboxylic acid isopropyl ester 
• 1160065-09-7 (S)-3-{(3-chloro-5-trifluoromethyl-benzyl)-[5-(1-methyl-1H-pyrazol-4-yl)-pyrimidin-2-yl]-amino}-pyrrolidine-1-carboxylic acid isopropyl ester 
• 955406-96-9 3-[2,6-Dichloro-4-(1-methyl-1H-pyrazol-4-yl)-benzyl]-1-(4,5,6,7-tetrahydro-2H-indazol-5-yl)-pyrrolidin-2-one 
• 955406-05-0 3-[2-Chloro-4-(1-methyl-1H-pyrazol-4-yl)-benzyl]-1-(4-oxo-cyclohexyl)-pyrrolidin-2-one 
• 1001917-37-8 MK-8033 
• 1001915-87-2 N-methyl-1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo-[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-phenylmethanesulfonamide 

Relevant articles and documents

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