1-methyl-1H-pyrazole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With C26H50CoN4O2 at 20℃; for 0.0833333h; Inert atmosphere; Glovebox; Stage #2: 1-methyl-1H-pyrazole at 80℃; for 48h; Inert atmosphere; Sealed tube; | 90% |
2,3-dimethyl-2,3-butane diol
(1-methyl-1H-pyrazol-5-yl)boronic acid
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With 4 A molecular sieve In tetrahydrofuran at 20℃; for 2h; | 84% |
In tetrahydrofuran at 20℃; for 48h; Molecular sieve; | 67% |
1-methyl-1H-pyrazole
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 0℃; for 1.25h; Stage #3: With ammonium chloride In tetrahydrofuran | 77% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at 0 - 20℃; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78℃; | 77% |
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 0℃; for 1.25h; | 77% |
Triisopropyl borate
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
Stage #1: 1-methyl-1H-pyrazole With n-butyllithium In tetrahydrofuran; hexanes at -78 - 20℃; for 1h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexanes for 1h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexanes | 51% |
3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
methyl iodide
A
1-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
B
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 70h; |
1-methyl-1H-pyrazole
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
A
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
B
1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
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; |
methyl 4-bromo-5-ethyl-2-thiophenecarboxylate
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
methyl 5-ethyl-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate
Conditions | Yield |
---|---|
With potassium carbonate; bis(tri-t-butylphosphine)palladium(0) at 80℃; for 1h; | 100% |
1,1-dimethylethyl (2-{[(5-bromo-3-thienyl)carbonyl]amino}-2-phenylethyl)carbamate
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
1,1-dimethylethyl [2-({[5-(1-methyl-1H-pyrazol-5-yl)-3-thienyl]carbonyl}amino)-2-phenylethyl]carbamate
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 17h; Suzuki Coupling; | 100% |
2-bromothiophene-4-carboxylic acid
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
5-(2-methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid
Conditions | Yield |
---|---|
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80℃; for 12 - 17h; Suzuki Coupling; | 100% |
N-(2-bromo-4-(trifluoromethyl)phenyl)acetamide
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water for 1h; Suzuki Coupling; Reflux; | 100% |
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water for 1h; Reflux; | 100% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In water at 110℃; for 3h; Inert atmosphere; | 100% |
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 130℃; for 0.333333h; Suzuki Coupling; Microwave irradiation; |
methyl 4-bromo-5-propyl-2-thiophenecarboxylate
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
methyl 4-(1-methyl-1H-pyrazol-5-yl)-5-propyl-2-thiophenecarboxylate
Conditions | Yield |
---|---|
With potassium carbonate; bis(tri-t-butylphosphine)palladium(0) at 80℃; for 1h; | 99% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
4-chloro-1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With N-chloro-succinimide; 2,4,6-trimethylaniline In dichloromethane at 20℃; for 24h; Inert atmosphere; | 99% |
With 2-chloro-1,3-bis(methoxycarbonyl)guanidine In acetonitrile at 20℃; for 12h; Reagent/catalyst; regioselective reaction; | 98% |
With N-chloro-succinimide; 2,2,6,6-tetramethylpiperidin-1-oxoammonium trifluoromethanesulfonate In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique; | 96% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In tetrahydrofuran; ethanol; water at 50℃; for 12h; Inert atmosphere; | 99% |
tert-butyl 1-(4-(2-chloro-7-phenylfuro[2,3-b]pyrazin-6-yl)phenyl)cyclobutylcarbamate
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
tert-butyl 1-(4-(2-(1-methyl-1H-pyrazol-5-yl)-7-phenylfuro[2,3-b]pyrazin-6-yl)phenyl)cyclobutylcarbamate
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 120℃; for 0.333333h; Microwave irradiation; Inert atmosphere; Sealed tube; | 98% |
2,4-dichloro-5-fluoropyrimidine
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In tetrahydrofuran; water Reflux; | 98% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
2-fluoro-9-(2-(isobutylamino)ethyl)-8-((6-(1-methyl-1H-pyrazol-5-yl)benzo[d][1,3]dioxol-5-yl)methyl)-9H-purin-6-amine
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride In water; N,N-dimethyl-formamide at 90℃; for 2h; Suzuki Coupling; Inert atmosphere; | 97% |
4-Bromo-3-methylbenzoic acid methyl ester
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; | 97% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
4-bromo-1-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With N-Bromosuccinimide; 2,4,6-trimethylaniline In dichloromethane at -40 - 0℃; for 24h; Inert atmosphere; regioselective reaction; | 96% |
2,6-Dichloropyrimidine
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium carbonate In 1,4-dioxane; water at 120℃; for 2h; | 96% |
5-bromo-1-(4-fluorophenyl)-3-(1-methylpiperidin-4-yl)-1H-indole
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
C24H25FN4
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 100℃; Suzuki-Miyaura Coupling; Inert atmosphere; | 95% |
4-methoxycarbonylphenyl bromide
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
methyl 4-(1-methyl-1H-pyrazol-5-yl)benzoate
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 0 - 120℃; Suzuki Coupling; Inert atmosphere; | 95% |
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; | 89% |
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 0 - 100℃; for 10h; Inert atmosphere; | 89% |
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 90℃; Suzuki Coupling; Inert atmosphere; | 85% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With potassium phosphate; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) In 1,4-dioxane; water at 80℃; for 18h; Inert atmosphere; | 95% |
4-bromo-2-fluoro-1-(methylsulfonyl)benzene
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere; | 94% |
5-bromo-3-methylpyridine-2-carboxylic acid methyl ester
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With potassium phosphate; tetrakis(triphenylphosphine) palladium(0) In N,N-dimethyl-formamide at 100℃; for 10h; Inert atmosphere; | 94% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 60℃; for 2h; | 94% |
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; dichloromethane; water at 60℃; for 2h; Suzuki Coupling; | 94% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
4-fluoro-N-methyl-N-{1-[4-(1-methyl-1H-pyrazole-5-yl)phthalazin-1-yl]piperidin-4-yl}-2-(trifluoromethyl)benzamide
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 74℃; for 12h; Suzuki Coupling; Inert atmosphere; | 92% |
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 74℃; for 12h; Suzuki Coupling; Inert atmosphere; | 92% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium phosphate tribasic trihydrate In N,N-dimethyl-formamide at 90℃; Inert atmosphere; | 92% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium hydrogencarbonate In 1,4-dioxane; water at 80℃; for 1h; Inert atmosphere; | 92% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro-[1,3-bis(2,6-diisopropylpenyl)-2-imidazolidinyliden]-(3-chloropyridyl)palladium(II); caesium carbonate In 1,4-dioxane; water; N,N-dimethyl-formamide at 90℃; for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation; | 91% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 100℃; Concentration; Inert atmosphere; | 91% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 140℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation; Sealed tube; | 91% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In methanol; water; toluene at 74℃; for 12h; Inert atmosphere; | 89% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Sealed tube; Microwave irradiation; | 89% |
1-methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole
Conditions | Yield |
---|---|
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); sodium carbonate In 1,4-dioxane; water at 25 - 80℃; for 2h; | 89% |
Molecule structure of 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester (CAS NO.847818-74-0):
Molecular Weight: 226.08 g/mol
Molecular Formula: C10H19BN2O3
Density: 1.06 g/cm3
Melting Point: 58-61 °C
Boiling Point: 355 °C at 760 mmHg
Flash Point: 168.5 °C
Index of Refraction: 1.485
Molar Refractivity: 61.15 cm3
Molar Volume: 213 cm3
Polarizability: 24.24×10-24 cm3
Surface Tension: 34 dyne/cm
Enthalpy of Vaporization: 63.32 kJ/mol
Vapour Pressure: 1.18E-05 mmHg at 25 °C
InChI: InChI=1/C10H19BN2O3/c1-9(2,14)10(3,4)16-11(15)8-6-7-12-13(8)5/h6-7,14-15H,1-5H3 Copy
InChIKey: KOSJKDRDKBVCGA-UHFFFAOYAV
Product Categories of 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester (CAS NO.847818-74-0): Boronic ester; Organoborons; Pyrazole
Hazard Codes: Xn
Risk Statements: 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
HazardClass: IRRITANT
1-Methyl-1H-pyrazole-5-boronic acid pinacol ester (CAS NO.847818-74-0) is also named as Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole ; 1H-Pyrazole,1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- ; 1-Methyl-1H-pyrazole-5-boronic acid pinacol ester, 97% ; 1H-pyrazole, 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxabo .
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